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Cheap flights from Houston to Chicago

Find cheap Chicago to Houston flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Houston.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
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Economy Class
  • Economy Class
  • Business Class
Done
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Houston to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Houston (HOU) - Chicago (CHI) 2026-09-04 2026-09-08 203 USD 21 hours 39 minutes Connection 2026-08-06T03:35:41
Houston (HOU) - Chicago (CHI) 2026-08-12 2026-09-01 246 USD 4 hours 45 minutes Direct 2026-08-09T16:46:15
Houston (HOU) - Chicago (CHI) 2026-09-18 2026-09-19 258 USD 4 hours 55 minutes Direct 2026-08-07T19:57:41
Houston (HOU) - Chicago (CHI) 2026-09-04 2026-09-07 269 USD 0 minutes Direct 2026-08-12T00:00:00
Houston (HOU) - Chicago (CHI) 2026-09-25 2026-09-28 276 USD 4 hours 50 minutes Direct 2026-08-06T02:20:53
Houston (HOU) - Chicago (CHI) 2026-09-18 2026-09-20 276 USD 0 minutes Direct 2026-08-12T00:00:00
Houston (HOU) - Chicago (CHI) 2026-09-18 2026-09-21 295 USD 18 hours 14 minutes Connection 2026-08-06T02:20:50
Houston (HOU) - Chicago (CHI) 2026-08-27 2026-08-30 321 USD 16 hours 39 minutes Connection 2026-08-06T02:20:47
Houston (HOU) - Chicago (CHI) 2026-09-04 2026-09-06 335 USD 16 hours 39 minutes Connection 2026-08-11T03:15:18
Houston (HOU) - Chicago (CHI) 2026-08-14 2026-08-16 477 USD 21 hours 10 minutes Connection 2026-08-11T02:48:21

Houston to Chicago flight status

Flight Origin Destination Departure Arrival Equip
FM9144 Houston (HOU) Chicago (MDW) 9:55 p.m. 12:15 a.m. 738
WN4318 Houston (HOU) Chicago (MDW) 8:10 a.m. 9:25 a.m. B737
WN3062 Houston (HOU) Chicago (MDW) 10:50 a.m. 12:10 p.m. B737
WN4804 Houston (HOU) Chicago (MDW) 4:55 p.m. 11:55 p.m. B738
WN3038 Houston (HOU) Chicago (MDW) 12:40 p.m. 2:15 p.m. B737
WN3550 Houston (HOU) Chicago (MDW) 7:30 p.m. 9:10 p.m. B738
WN4528 Houston (HOU) Chicago (MDW) 3:30 p.m. 5:30 p.m. B738
WN4265 Houston (HOU) Chicago (MDW) 9:05 p.m. 10:30 p.m. B737
WN4554 Houston (HOU) Chicago (MDW) 9:05 p.m. 10:25 p.m. B737
WN3616 Houston (HOU) Chicago (MDW) 12:20 p.m. 4:10 p.m. B737
WN4134 Houston (HOU) Chicago (MDW) 11:30 a.m. 1:20 p.m. B737
WN2299 Houston (HOU) Chicago (MDW) 4:55 p.m. 6:50 p.m. B738
WN5109 Houston (HOU) Chicago (MDW) 1:35 p.m. 2:45 p.m. B737
WN6181 Houston (HOU) Chicago (MDW) 6:15 a.m. 7:05 a.m. B737
EO680 Houston (HOU) Chicago (MDW) 6 a.m. 7:45 a.m. 320
FL294 Houston (HOU) Chicago (MDW) 7 p.m. 8 p.m.
HG3883 Houston (HOU) Chicago (MDW) 9:55 a.m. 11:50 a.m.
FL8765 Houston (HOU) Chicago (MDW) 9:40 p.m. 11 p.m.
FO105 Houston (HOU) Chicago (MDW) 7:15 a.m. 1:20 p.m. CR2

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