Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Houston to Chicago is Spirit Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Houston to Chicago is May.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
Cheapest Day of the Week
Saturday
The cheapest day(s) of the week to fly from Houston to Chicago is Saturday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Cheapest Time
9pm
The cheapest time of the day to fly from Houston to Chicago is in the evening.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Earliest
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Filter by Airline
All
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Total Duration
- Shortest
- Longest
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Stopover
All
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Availability
- M
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- S
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19:40 - 22:10IAH - ORD
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19:40 (IAH)Houston George Bush Intercontinental Airport
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22:10 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2183)Boeing 737 900 - 2h 30m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
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20:10 - 22:40HOU - MDW
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20:10 (HOU)Houston Hobby Airport
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22:40 (MDW)Chicago Midway Airport
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(WN 3115)Boeing 737 700 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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20:40 - 23:15HOU - MDW
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20:40 (HOU)Houston Hobby Airport
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23:15 (MDW)Chicago Midway Airport
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(WN 3115)Boeing 737 700 - 2h 35m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
20:50 - 23:25HOU - MDW
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20:50 (HOU)Houston Hobby Airport
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23:25 (MDW)Chicago Midway Airport
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(WN 3115)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
21:35 - 00:05+ 1HOU - MDW
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21:35 (HOU)Houston Hobby Airport
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00:05 (MDW)Chicago Midway Airport + 1
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(WN 3115)Boeing 737 800 - 2h 30m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
-
21:40 - 00:10+ 1IAH - ORD
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21:40 (IAH)Houston George Bush Intercontinental Airport
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00:10 (ORD)Chicago O'Hare International Airport + 1
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United Airlines (UA 750)Boeing 737 800 - 2h 30m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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05:05 - 07:30HOU - MDW
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05:05 (HOU)Houston Hobby Airport
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07:30 (MDW)Chicago Midway Airport
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(WN 5487)Boeing 737 800 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
05:24 - 08:04IAH - ORD
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05:24 (IAH)Houston George Bush Intercontinental Airport
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08:04 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2653)Boeing 737 800 - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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05:25 - 07:50HOU - MDW
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05:25 (HOU)Houston Hobby Airport
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07:50 (MDW)Chicago Midway Airport
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(WN 5487)Boeing 737 700 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
05:30 - 07:55HOU - MDW
-
05:30 (HOU)Houston Hobby Airport
-
07:55 (MDW)Chicago Midway Airport
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(WN 5487)Boeing 737 Max 8 Passenger - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
06:30 - 09:00HOU - MDW
-
06:30 (HOU)Houston Hobby Airport
-
09:00 (MDW)Chicago Midway Airport
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(WN 5791)Boeing 737 700 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
06:45 - 09:25IAH - ORD
-
06:45 (IAH)Houston George Bush Intercontinental Airport
-
09:25 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 247)Boeing 737 800 - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
07:25 - 10:00IAH - ORD
-
07:25 (IAH)Houston George Bush Intercontinental Airport
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10:00 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 469)Boeing 737 900 - 2h 35m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
08:00 - 10:35HOU - MDW
-
08:00 (HOU)Houston Hobby Airport
-
10:35 (MDW)Chicago Midway Airport
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(WN 6128)Boeing 737 700 - 2h 35m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
08:05 - 15:41IAH - ORD
-
08:05 (IAH)Houston George Bush Intercontinental Airport
-
15:41 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2649)Airbus - 7h 36m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
-
08:20 - 11:00HOU - MDW
-
08:20 (HOU)Houston Hobby Airport
-
11:00 (MDW)Chicago Midway Airport
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(WN 6128)Boeing 737 800 - 2h 40m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
-
08:35 - 11:10HOU - MDW
-
08:35 (HOU)Houston Hobby Airport
-
11:10 (MDW)Chicago Midway Airport
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(WN 6128)Boeing 737 700 - 2h 35m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
08:35 - 12:35HOU - MDW
-
08:35 (HOU)Houston Hobby Airport
-
12:35 (MDW)Chicago Midway Airport
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(WN 1791)Boeing 737 700 - 4h
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
08:55 - 11:30HOU - MDW
-
08:55 (HOU)Houston Hobby Airport
-
11:30 (MDW)Chicago Midway Airport
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(WN 6128)Boeing 737 700 - 2h 35m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
09:00 - 11:20IAH - MDW
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09:00 (IAH)Houston George Bush Intercontinental Airport
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11:20 (MDW)Chicago Midway Airport
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(WN 3116)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
09:05 - 11:25IAH - MDW
-
09:05 (IAH)Houston George Bush Intercontinental Airport
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11:25 (MDW)Chicago Midway Airport
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(WN 3116)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
09:35 - 12:16IAH - ORD
-
09:35 (IAH)Houston George Bush Intercontinental Airport
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12:16 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2282)Boeing 737 900 - 2h 41m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
11:25 - 13:45IAH - MDW
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11:25 (IAH)Houston George Bush Intercontinental Airport
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13:45 (MDW)Chicago Midway Airport
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(WN 5795)Boeing 737 700 - 2h 20m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
11:36 - 14:20IAH - ORD
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11:36 (IAH)Houston George Bush Intercontinental Airport
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14:20 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1636)Boeing 737 800 - 2h 44m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
11:40 - 14:10HOU - MDW
-
11:40 (HOU)Houston Hobby Airport
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14:10 (MDW)Chicago Midway Airport
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(WN 460)Boeing 737 700 - 2h 30m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
11:55 - 22:55IAH - ORD
-
11:55 (IAH)Houston George Bush Intercontinental Airport
-
22:55 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1371)Boeing 737 800 - 11h
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
12:00 - 22:49IAH - ORD
-
12:00 (IAH)Houston George Bush Intercontinental Airport
-
22:49 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2486)Boeing 737 900 - 10h 49m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
12:10 - 14:50IAH - ORD
-
12:10 (IAH)Houston George Bush Intercontinental Airport
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14:50 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1168)Boeing 737 900 - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
12:40 - 15:05IAH - MDW
-
12:40 (IAH)Houston George Bush Intercontinental Airport
-
15:05 (MDW)Chicago Midway Airport
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(WN 549)Boeing 737 700 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
13:10 - 15:35IAH - MDW
-
13:10 (IAH)Houston George Bush Intercontinental Airport
-
15:35 (MDW)Chicago Midway Airport
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(WN 549)Boeing 737 800 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
-
13:15 - 15:40IAH - MDW
-
13:15 (IAH)Houston George Bush Intercontinental Airport
-
15:40 (MDW)Chicago Midway Airport
-
(WN 549)Boeing 737 700 - 2h 25m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
13:35 - 16:00HOU - MDW
-
13:35 (HOU)Houston Hobby Airport
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16:00 (MDW)Chicago Midway Airport
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(WN 5388)Boeing 737 700 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
14:10 - 18:10HOU - MDW
-
14:10 (HOU)Houston Hobby Airport
-
18:10 (MDW)Chicago Midway Airport
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(WN 500)Boeing 737 700 - 4h
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
14:10 - 18:20HOU - MDW
-
14:10 (HOU)Houston Hobby Airport
-
18:20 (MDW)Chicago Midway Airport
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(WN 1506)Boeing 737 700 - 4h 10m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
14:15 - 16:40HOU - MDW
-
14:15 (HOU)Houston Hobby Airport
-
16:40 (MDW)Chicago Midway Airport
-
(WN 3970)Boeing 737 700 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
14:20 - 16:45HOU - MDW
-
14:20 (HOU)Houston Hobby Airport
-
16:45 (MDW)Chicago Midway Airport
-
(WN 3970)Boeing 737 Max 8 Passenger - 2h 25m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
14:20 - 17:08IAH - ORD
-
14:20 (IAH)Houston George Bush Intercontinental Airport
-
17:08 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 787)Boeing 737 900 - 2h 48m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
14:20 - 19:45HOU - MDW
-
14:20 (HOU)Houston Hobby Airport
-
19:45 (MDW)Chicago Midway Airport
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(WN 2381)Boeing 737 700 - 5h 25m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
14:50 - 19:59IAH - ORD
-
14:50 (IAH)Houston George Bush Intercontinental Airport
-
19:59 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2220)Boeing 737 800 - 5h 09m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
15:01 - 17:45IAH - ORD
-
15:01 (IAH)Houston George Bush Intercontinental Airport
-
17:45 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1168)Boeing 737 800 - 2h 44m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
15:30 - 17:55IAH - MDW
-
15:30 (IAH)Houston George Bush Intercontinental Airport
-
17:55 (MDW)Chicago Midway Airport
-
(WN 3118)Boeing 737 700 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- S
- Boeing 737 700
-
15:45 - 19:40HOU - MDW
-
15:45 (HOU)Houston Hobby Airport
-
19:40 (MDW)Chicago Midway Airport
-
(WN 2644)Boeing 737 700 - 3h 55m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
15:45 - 20:30HOU - MDW
-
15:45 (HOU)Houston Hobby Airport
-
20:30 (MDW)Chicago Midway Airport
-
(WN 2896)Boeing 737 700 - 4h 45m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
16:05 - 18:35IAH - MDW
-
16:05 (IAH)Houston George Bush Intercontinental Airport
-
18:35 (MDW)Chicago Midway Airport
-
(WN 3118)Boeing 737 800 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
16:05 - 20:10HOU - MDW
-
16:05 (HOU)Houston Hobby Airport
-
20:10 (MDW)Chicago Midway Airport
-
(WN 1378)Boeing 737 700 - 4h 05m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
16:30 - 19:14IAH - ORD
-
16:30 (IAH)Houston George Bush Intercontinental Airport
-
19:14 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2406)Boeing 737 900 - 2h 44m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
16:35 - 19:00HOU - MDW
-
16:35 (HOU)Houston Hobby Airport
-
19:00 (MDW)Chicago Midway Airport
-
(WN 3114)Boeing 737 700 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
16:55 - 19:30HOU - MDW
-
16:55 (HOU)Houston Hobby Airport
-
19:30 (MDW)Chicago Midway Airport
-
(WN 3114)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
18:15 - 20:45HOU - MDW
-
18:15 (HOU)Houston Hobby Airport
-
20:45 (MDW)Chicago Midway Airport
-
(WN 3114)Boeing 737 700 - 2h 30m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
18:20 - 21:11IAH - ORD
-
18:20 (IAH)Houston George Bush Intercontinental Airport
-
21:11 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 520)Boeing 737 800 - 2h 51m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
Connecting Flights
-
19:00 - 20:20HOU - DAL21:10 - 23:20DAL - MDW
-
19:00 (HOU)Houston Hobby Airport21:10 (DAL)Dallas/Fort Worth Love Field Airport
-
20:20 (DAL)Dallas/Fort Worth Love Field Airport23:20 (MDW)Chicago Midway Airport
-
(WN 52)Boeing 737 800 (WN 3084)Boeing 737 800 - 4h 20m (50m)
- DAL Dallas 50m
-
- -
- T
- W
- -
- -
- -
- -
-
19:00 - 20:15+ 1HOU - DAL22:00 - 00:10+ 1DAL - MDW
-
19:00 (HOU)Houston Hobby Airport22:00 (DAL)Dallas/Fort Worth Love Field Airport
-
20:15 (DAL)Dallas/Fort Worth Love Field Airport + 100:10 (MDW)Chicago Midway Airport
-
(WN 52)Boeing 737 700 (WN 3084)Boeing 737 800 - 5h 10m (1h 45m)
- DAL Dallas 1h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
19:20 - 20:20HOU - AUS21:05 - 23:35AUS - MDW
-
19:20 (HOU)Houston Hobby Airport21:05 (AUS)Austin-Bergstrom International Airport
-
20:20 (AUS)Austin-Bergstrom International Airport23:35 (MDW)Chicago Midway Airport
-
(WN 402)Boeing 737 800 (WN 6085)Boeing 737 800 - 4h 15m (45m)
- AUS Austin 45m
-
- -
- T
- W
- -
- -
- -
- -
-
20:00 - 21:15+ 1HOU - DAL22:00 - 00:10+ 1DAL - MDW
-
20:00 (HOU)Houston Hobby Airport22:00 (DAL)Dallas/Fort Worth Love Field Airport
-
21:15 (DAL)Dallas/Fort Worth Love Field Airport + 100:10 (MDW)Chicago Midway Airport
-
(WN 58)Boeing 737 700 (WN 3084)Boeing 737 800 - 4h 10m (45m)
- DAL Dallas 45m
-
- M
- -
- -
- T
- F
- -
- -
-
05:25 - 08:40HOU - MCO09:40 - 11:25MCO - MDW
-
05:25 (HOU)Houston Hobby Airport09:40 (MCO)Orlando International Airport
-
08:40 (MCO)Orlando International Airport11:25 (MDW)Chicago Midway Airport
-
(WN 5733)Boeing 737 800 (WN 3156)Boeing 737 800 - 6h (1h)
- MCO Orlando 1h
-
- M
- -
- -
- T
- F
- -
- -
-
05:40 - 08:50HOU - TPA09:35 - 11:15TPA - MDW
-
05:40 (HOU)Houston Hobby Airport09:35 (TPA)Tampa International Airport
-
08:50 (TPA)Tampa International Airport11:15 (MDW)Chicago Midway Airport
-
(WN 6034)Boeing 737 700 (WN 3246)Boeing 737 700 - 5h 35m (45m)
- TPA Tampa 45m
-
- M
- -
- -
- T
- F
- -
- -
-
05:40 - 08:55HOU - MCO09:45 - 11:30MCO - MDW
-
05:40 (HOU)Houston Hobby Airport09:45 (MCO)Orlando International Airport
-
08:55 (MCO)Orlando International Airport11:30 (MDW)Chicago Midway Airport
-
(WN 5733)Boeing 737 700 (WN 3156)Boeing 737 800 - 5h 50m (50m)
- MCO Orlando 50m
-
- -
- T
- W
- -
- -
- -
- -
-
05:40 - 08:55HOU - MCO09:30 - 11:30MCO - ORD
-
05:40 (HOU)Houston Hobby Airport09:30 (MCO)Orlando International Airport
-
08:55 (MCO)Orlando International Airport11:30 (ORD)Chicago O'Hare International Airport
-
(WN 5733)Boeing 737 700 (WN 934)Boeing 737 800 - 5h 50m (35m)
- MCO Orlando 35m
-
- -
- T
- W
- -
- -
- -
- -
-
05:45 - 06:45IAH - DAL07:30 - 09:40DAL - MDW
-
05:45 (IAH)Houston George Bush Intercontinental Airport07:30 (DAL)Dallas/Fort Worth Love Field Airport
-
06:45 (DAL)Dallas/Fort Worth Love Field Airport09:40 (MDW)Chicago Midway Airport
-
(WN 5571)Boeing 737 800 (WN 3079)Boeing 737 Max 8 Passenger - 3h 55m (45m)
- DAL Dallas 45m
-
- M
- -
- -
- T
- F
- -
- -
-
05:45 - 06:45IAH - DAL09:10 - 11:30DAL - ORD
-
05:45 (IAH)Houston George Bush Intercontinental Airport09:10 (DAL)Dallas/Fort Worth Love Field Airport
-
06:45 (DAL)Dallas/Fort Worth Love Field Airport11:30 (ORD)Chicago O'Hare International Airport
-
(WN 5571)Boeing 737 800 (WN 4903)Boeing 737 800 - 5h 45m (2h 25m)
- DAL Dallas 2h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
05:45 - 07:40HOU - STL10:00 - 11:05STL - MDW
-
05:45 (HOU)Houston Hobby Airport10:00 (STL)St Louis Lambert Intl Airport
-
07:40 (STL)St Louis Lambert Intl Airport11:05 (MDW)Chicago Midway Airport
-
(WN 4649)Boeing 737 700 (WN 5866)Boeing 737 Max 8 Passenger - 5h 20m (2h 20m)
- STL Saint Louis 2h 20m
-
- -
- -
- -
- -
- -
- -
- S
-
05:45 - 07:45HOU - STL09:45 - 10:50STL - MDW
-
05:45 (HOU)Houston Hobby Airport09:45 (STL)St Louis Lambert Intl Airport
-
07:45 (STL)St Louis Lambert Intl Airport10:50 (MDW)Chicago Midway Airport
-
(WN 4649)Boeing 737 Max 8 Passenger (WN 4631)Boeing 737 700 - 5h 05m (2h)
- STL Saint Louis 2h
-
- -
- T
- W
- -
- -
- -
- -
-
05:50 - 07:25HOU - DEN08:25 - 11:50DEN - ORD
-
05:50 (HOU)Houston Hobby Airport08:25 (DEN)Denver Intl Airport
-
07:25 (DEN)Denver Intl Airport11:50 (ORD)Chicago O'Hare International Airport
-
(WN 175)Boeing 737 700 (WN 941)Boeing 737 700 - 6h (1h)
- DEN Denver 1h
-
- M
- -
- -
- T
- F
- -
- -
-
06:00 - 07:00IAH - DAL09:05 - 11:20DAL - MDW
-
06:00 (IAH)Houston George Bush Intercontinental Airport09:05 (DAL)Dallas/Fort Worth Love Field Airport
-
07:00 (DAL)Dallas/Fort Worth Love Field Airport11:20 (MDW)Chicago Midway Airport
-
(WN 5571)Boeing 737 800 (WN 2148)Boeing 737 800 - 5h 20m (2h 05m)
- DAL Dallas 2h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 07:05HOU - DAL09:10 - 11:30DAL - ORD
-
06:00 (HOU)Houston Hobby Airport09:10 (DAL)Dallas/Fort Worth Love Field Airport
-
07:05 (DAL)Dallas/Fort Worth Love Field Airport11:30 (ORD)Chicago O'Hare International Airport
-
(WN 1636)Boeing 737 700 (WN 4903)Boeing 737 800 - 5h 30m (2h 05m)
- DAL Dallas 2h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
06:00 - 07:05HOU - DAL09:05 - 11:20DAL - MDW
-
06:00 (HOU)Houston Hobby Airport09:05 (DAL)Dallas/Fort Worth Love Field Airport
-
07:05 (DAL)Dallas/Fort Worth Love Field Airport11:20 (MDW)Chicago Midway Airport
-
(WN 1636)Boeing 737 Max 8 Passenger (WN 2148)Boeing 737 800 - 5h 20m (2h)
- DAL Dallas 2h
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 09:00HOU - ATL10:45 - 11:40ATL - MDW
-
06:05 (HOU)Houston Hobby Airport10:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:40 (MDW)Chicago Midway Airport
-
(WN 5096)Boeing 737 Max 8 Passenger (WN 5518)Boeing 737 Max 8 Passenger - 5h 35m (1h 45m)
- ATL Atlanta 1h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
06:10 - 07:35IAH - DEN09:00 - 12:20DEN - MDW
-
06:10 (IAH)Houston George Bush Intercontinental Airport09:00 (DEN)Denver Intl Airport
-
07:35 (DEN)Denver Intl Airport12:20 (MDW)Chicago Midway Airport
-
(WN 5657)Boeing 737 800 (WN 5584)Boeing 737 800 - 6h 10m (1h 25m)
- DEN Denver 1h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
06:10 - 07:35IAH - DEN08:25 - 11:50DEN - ORD
-
06:10 (IAH)Houston George Bush Intercontinental Airport08:25 (DEN)Denver Intl Airport
-
07:35 (DEN)Denver Intl Airport11:50 (ORD)Chicago O'Hare International Airport
-
(WN 5657)Boeing 737 800 (WN 941)Boeing 737 700 - 5h 40m (50m)
- DEN Denver 50m
-
- M
- -
- -
- T
- F
- -
- -
-
06:15 - 09:15HOU - TPA09:55 - 11:50TPA - ORD
-
06:15 (HOU)Houston Hobby Airport09:55 (TPA)Tampa International Airport
-
09:15 (TPA)Tampa International Airport11:50 (ORD)Chicago O'Hare International Airport
-
(WN 6034)Boeing 737 700 (WN 2163)Boeing 737 700 - 5h 35m (40m)
- TPA Tampa 40m
-
- -
- -
- -
- -
- -
- -
- S
-
06:15 - 07:40HOU - DEN08:25 - 11:50DEN - ORD
-
06:15 (HOU)Houston Hobby Airport08:25 (DEN)Denver Intl Airport
-
07:40 (DEN)Denver Intl Airport11:50 (ORD)Chicago O'Hare International Airport
-
(WN 1625)Boeing 737 Max 8 Passenger (WN 941)Boeing 737 700 - 5h 35m (45m)
- DEN Denver 45m
-
- -
- T
- W
- -
- -
- -
- -
-
06:15 - 07:40HOU - DEN08:25 - 11:45DEN - MDW
-
06:15 (HOU)Houston Hobby Airport08:25 (DEN)Denver Intl Airport
-
07:40 (DEN)Denver Intl Airport11:45 (MDW)Chicago Midway Airport
-
(WN 1625)Boeing 737 Max 8 Passenger (WN 692)Boeing 737 800 - 5h 30m (45m)
- DEN Denver 45m
-
- -
- -
- -
- -
- -
- S
- -
-
06:20 - 07:25IAH - DAL09:40 - 11:50DAL - MDW
-
06:20 (IAH)Houston George Bush Intercontinental Airport09:40 (DAL)Dallas/Fort Worth Love Field Airport
-
07:25 (DAL)Dallas/Fort Worth Love Field Airport11:50 (MDW)Chicago Midway Airport
-
(WN 5571)Boeing 737 Max 8 Passenger (WN 2148)Boeing 737 Max 8 Passenger - 5h 30m (2h 15m)
- DAL Dallas 2h 15m
-
- -
- -
- -
- -
- -
- S
- -
-
06:30 - 08:25HOU - MCI10:40 - 12:05MCI - MDW
-
06:30 (HOU)Houston Hobby Airport10:40 (MCI)Kansas City International Airport
-
08:25 (MCI)Kansas City International Airport12:05 (MDW)Chicago Midway Airport
-
(WN 454)Boeing 737 Max 8 Passenger (WN 4988)Boeing 737 700 - 5h 35m (2h 15m)
- MCI 2h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
06:35 - 09:55HOU - FLL10:55 - 13:00FLL - MDW
-
06:35 (HOU)Houston Hobby Airport10:55 (FLL)Fort Lauderdale/Hollywood Intl Airport
-
09:55 (FLL)Fort Lauderdale/Hollywood Intl Airport13:00 (MDW)Chicago Midway Airport
-
(WN 5384)Boeing 737 700 (WN 3684)Boeing 737 800 - 6h 25m (1h)
- FLL Miami 1h
-
- -
- -
- -
- -
- -
- S
- -
-
06:40 - 09:35HOU - ATL10:40 - 11:35ATL - MDW
-
06:40 (HOU)Houston Hobby Airport10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:35 (MDW)Chicago Midway Airport
-
(WN 5096)Boeing 737 700 (WN 5518)Boeing 737 Max 8 Passenger - 4h 55m (1h 05m)
- ATL Atlanta 1h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
06:45 - 09:55HOU - TPA11:20 - 13:00TPA - MDW
-
06:45 (HOU)Houston Hobby Airport11:20 (TPA)Tampa International Airport
-
09:55 (TPA)Tampa International Airport13:00 (MDW)Chicago Midway Airport
-
(WN 6034)Boeing 737 700 (WN 3493)Boeing 737 Max 8 Passenger - 6h 15m (1h 25m)
- TPA Tampa 1h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
06:55 - 08:00HOU - DAL09:40 - 11:50DAL - MDW
-
06:55 (HOU)Houston Hobby Airport09:40 (DAL)Dallas/Fort Worth Love Field Airport
-
08:00 (DAL)Dallas/Fort Worth Love Field Airport11:50 (MDW)Chicago Midway Airport
-
(WN 4)Boeing 737 800 (WN 2148)Boeing 737 Max 8 Passenger - 4h 55m (1h 40m)
- DAL Dallas 1h 40m
-
- -
- -
- -
- -
- -
- S
- -
-
07:00 - 08:15HOU - DAL10:45 - 13:05DAL - ORD
-
07:00 (HOU)Houston Hobby Airport10:45 (DAL)Dallas/Fort Worth Love Field Airport
-
08:15 (DAL)Dallas/Fort Worth Love Field Airport13:05 (ORD)Chicago O'Hare International Airport
-
(WN 4)Boeing 737 800 (WN 4903)Boeing 737 700 - 6h 05m (2h 30m)
- DAL Dallas 2h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
07:00 - 08:20HOU - DAL11:00 - 13:10DAL - MDW
-
07:00 (HOU)Houston Hobby Airport11:00 (DAL)Dallas/Fort Worth Love Field Airport
-
08:20 (DAL)Dallas/Fort Worth Love Field Airport13:10 (MDW)Chicago Midway Airport
-
(WN 4)Boeing 737 800 (WN 2148)Boeing 737 Max 8 Passenger - 6h 10m (2h 40m)
- DAL Dallas 2h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
07:00 - 08:15HOU - DAL09:05 - 11:20DAL - MDW
-
07:00 (HOU)Houston Hobby Airport09:05 (DAL)Dallas/Fort Worth Love Field Airport
-
08:15 (DAL)Dallas/Fort Worth Love Field Airport11:20 (MDW)Chicago Midway Airport
-
(WN 4)Boeing 737 800 (WN 2148)Boeing 737 800 - 4h 20m (50m)
- DAL Dallas 50m
-
- -
- T
- W
- -
- -
- -
- -
-
07:00 - 08:20HOU - DAL09:10 - 11:30DAL - ORD
-
07:00 (HOU)Houston Hobby Airport09:10 (DAL)Dallas/Fort Worth Love Field Airport
-
08:20 (DAL)Dallas/Fort Worth Love Field Airport11:30 (ORD)Chicago O'Hare International Airport
-
(WN 4)Boeing 737 800 (WN 4903)Boeing 737 800 - 4h 30m (50m)
- DAL Dallas 50m
-
- M
- -
- -
- T
- F
- -
- -
-
07:05 - 09:00IAH - BNA11:00 - 12:45BNA - ORD
-
07:05 (IAH)Houston George Bush Intercontinental Airport11:00 (BNA)Nashville Airport
-
09:00 (BNA)Nashville Airport12:45 (ORD)Chicago O'Hare International Airport
-
(WN 586)Boeing 737 800 (WN 3624)Boeing 737 800 - 5h 40m (2h)
- BNA Nashville 2h
-
- -
- -
- -
- -
- -
- -
- S
-
07:20 - 09:25HOU - BNA10:15 - 12:00BNA - ORD
-
07:20 (HOU)Houston Hobby Airport10:15 (BNA)Nashville Airport
-
09:25 (BNA)Nashville Airport12:00 (ORD)Chicago O'Hare International Airport
-
(WN 4941)Boeing 737 Max 8 Passenger (WN 3624)Boeing 737 700 - 4h 40m (50m)
- BNA Nashville 50m
-
- -
- -
- -
- -
- -
- S
- -
-
07:25 - 08:40HOU - DAL11:35 - 13:45DAL - MDW
-
07:25 (HOU)Houston Hobby Airport11:35 (DAL)Dallas/Fort Worth Love Field Airport
-
08:40 (DAL)Dallas/Fort Worth Love Field Airport13:45 (MDW)Chicago Midway Airport
-
(WN 4)Boeing 737 Max 8 Passenger (WN 2148)Boeing 737 Max 8 Passenger - 6h 20m (2h 55m)
- DAL Dallas 2h 55m
-
- -
- -
- -
- -
- -
- -
- S
-
07:30 - 08:45HOU - MSY10:10 - 12:30MSY - MDW
-
07:30 (HOU)Houston Hobby Airport10:10 (MSY)New Orleans Louis Armstrong Intl Airport
-
08:45 (MSY)New Orleans Louis Armstrong Intl Airport12:30 (MDW)Chicago Midway Airport
-
(WN 3373)Boeing 737 700 (WN 1704)Boeing 737 700 - 5h (1h 25m)
- MSY New Orleans 1h 25m
-
- -
- -
- -
- -
- -
- S
- -
-
07:40 - 08:55HOU - DAL09:40 - 11:50DAL - MDW
-
07:40 (HOU)Houston Hobby Airport09:40 (DAL)Dallas/Fort Worth Love Field Airport
-
08:55 (DAL)Dallas/Fort Worth Love Field Airport11:50 (MDW)Chicago Midway Airport
-
(WN 6)Boeing 737 Max 8 Passenger (WN 2148)Boeing 737 Max 8 Passenger - 4h 10m (45m)
- DAL Dallas 45m
-
- -
- -
- -
- -
- -
- S
- -
-
07:40 - 09:40HOU - MCI10:20 - 11:45MCI - MDW
-
07:40 (HOU)Houston Hobby Airport10:20 (MCI)Kansas City International Airport
-
09:40 (MCI)Kansas City International Airport11:45 (MDW)Chicago Midway Airport
-
(WN 4521)Boeing 737 700 (WN 4988)Boeing 737 700 - 4h 05m (40m)
- MCI 40m
-
- -
- T
- W
- -
- -
- -
- -
-
07:55 - 09:25IAH - DEN10:35 - 13:55DEN - MDW
-
07:55 (IAH)Houston George Bush Intercontinental Airport10:35 (DEN)Denver Intl Airport
-
09:25 (DEN)Denver Intl Airport13:55 (MDW)Chicago Midway Airport
-
(WN 5657)Boeing 737 Max 8 Passenger (WN 878)Boeing 737 700 - 6h (1h 10m)
- DEN Denver 1h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
08:00 - 09:40HOU - DEN10:25 - 13:40DEN - MDW
-
08:00 (HOU)Houston Hobby Airport10:25 (DEN)Denver Intl Airport
-
09:40 (DEN)Denver Intl Airport13:40 (MDW)Chicago Midway Airport
-
(WN 2352)Boeing 737 Max 8 Passenger (WN 2503)Boeing 737 800 - 5h 40m (45m)
- DEN Denver 45m
-
- -
- T
- W
- -
- -
- -
- -
-
08:20 - 10:30HOU - STL12:35 - 13:40STL - MDW
-
08:20 (HOU)Houston Hobby Airport12:35 (STL)St Louis Lambert Intl Airport
-
10:30 (STL)St Louis Lambert Intl Airport13:40 (MDW)Chicago Midway Airport
-
(WN 749)Boeing 737 Max 8 Passenger (WN 3241)Boeing 737 700 - 5h 20m (2h 05m)
- STL Saint Louis 2h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 09:45HOU - DAL10:45 - 13:05DAL - ORD
-
08:30 (HOU)Houston Hobby Airport10:45 (DAL)Dallas/Fort Worth Love Field Airport
-
09:45 (DAL)Dallas/Fort Worth Love Field Airport13:05 (ORD)Chicago O'Hare International Airport
-
(WN 10)Boeing 737 700 (WN 4903)Boeing 737 700 - 4h 35m (1h)
- DAL Dallas 1h
-
- -
- T
- W
- -
- -
- -
- -
-
08:30 - 09:45HOU - DAL12:35 - 14:45DAL - MDW
-
08:30 (HOU)Houston Hobby Airport12:35 (DAL)Dallas/Fort Worth Love Field Airport
-
09:45 (DAL)Dallas/Fort Worth Love Field Airport14:45 (MDW)Chicago Midway Airport
-
(WN 10)Boeing 737 700 (WN 473)Boeing 737 Max 8 Passenger - 6h 15m (2h 50m)
- DAL Dallas 2h 50m
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 09:45HOU - DAL11:00 - 13:10DAL - MDW
-
08:30 (HOU)Houston Hobby Airport11:00 (DAL)Dallas/Fort Worth Love Field Airport
-
09:45 (DAL)Dallas/Fort Worth Love Field Airport13:10 (MDW)Chicago Midway Airport
-
(WN 10)Boeing 737 700 (WN 2148)Boeing 737 Max 8 Passenger - 4h 40m (1h 15m)
- DAL Dallas 1h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 09:45HOU - DAL11:55 - 14:10DAL - MDW
-
08:30 (HOU)Houston Hobby Airport11:55 (DAL)Dallas/Fort Worth Love Field Airport
-
09:45 (DAL)Dallas/Fort Worth Love Field Airport14:10 (MDW)Chicago Midway Airport
-
(WN 10)Boeing 737 700 (WN 473)Boeing 737 800 - 5h 40m (2h 10m)
- DAL Dallas 2h 10m
-
- -
- T
- W
- -
- -
- -
- -
-
08:35 - 09:35HOU - AUS10:50 - 13:20AUS - MDW
-
08:35 (HOU)Houston Hobby Airport10:50 (AUS)Austin-Bergstrom International Airport
-
09:35 (AUS)Austin-Bergstrom International Airport13:20 (MDW)Chicago Midway Airport
-
(WN 2842)Boeing 737 800 (WN 3033)Boeing 737 700 - 4h 45m (1h 15m)
- AUS Austin 1h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
08:35 - 12:05HOU - MCO13:05 - 14:50MCO - MDW
-
08:35 (HOU)Houston Hobby Airport13:05 (MCO)Orlando International Airport
-
12:05 (MCO)Orlando International Airport14:50 (MDW)Chicago Midway Airport
-
(WN 5084)Boeing 737 Max 8 Passenger (WN 3157)Boeing 737 Max 8 Passenger - 6h 15m (1h)
- MCO Orlando 1h
-
- -
- T
- W
- -
- -
- -
- -
-
08:40 - 11:55IAH - MCO12:40 - 14:25MCO - MDW
-
08:40 (IAH)Houston George Bush Intercontinental Airport12:40 (MCO)Orlando International Airport
-
11:55 (MCO)Orlando International Airport14:25 (MDW)Chicago Midway Airport
-
(WN 2975)Boeing 737 800 (WN 3157)Boeing 737 Max 8 Passenger - 5h 45m (45m)
- MCO Orlando 45m
-
- -
- -
- -
- -
- -
- S
- -
-
08:40 - 10:00HOU - MSY12:35 - 14:55MSY - MDW
-
08:40 (HOU)Houston Hobby Airport12:35 (MSY)New Orleans Louis Armstrong Intl Airport
-
10:00 (MSY)New Orleans Louis Armstrong Intl Airport14:55 (MDW)Chicago Midway Airport
-
(WN 3373)Boeing 737 Max 8 Passenger (WN 2055)Boeing 737 Max 8 Passenger - 6h 15m (2h 35m)
- MSY New Orleans 2h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
08:45 - 09:45HOU - AUS11:10 - 13:40AUS - MDW
-
08:45 (HOU)Houston Hobby Airport11:10 (AUS)Austin-Bergstrom International Airport
-
09:45 (AUS)Austin-Bergstrom International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 2842)Boeing 737 700 (WN 3033)Boeing 737 800 - 4h 55m (1h 25m)
- AUS Austin 1h 25m
-
- M
- -
- -
- T
- F
- -
- -
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What’s the fastest flight time from Houston to Chicago?
The fastest flight time for direct flights from Houston to Chicago is 2 hours 20 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Houston to Chicago?
The most popular airline flying from Houston to Chicago is American Airlines. Find the latest flight deals on Wego.
How far is Chicago from Houston?
The flight distance between Houston and Chicago is 1516km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 05:05. The last flight of the day departs at 19:00. See the full list of flight times on Wego.
How many airlines offer direct flights from Houston to Chicago?
There are 3 airlines that offer direct flights from Houston to Chicago. Find out the list of airlines on Wego.
All Airports in Chicago
Popular Airlines flying from Houston to Chicago
Popular destinations from Chicago
Popular destinations from Houston
Popular Hotels in Chicago
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- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
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