Cheap flights from Houston to Chicago
Recently found return fares from $137, with October the cheapest month we know of. Compare dates, then book with the partner you choose.
Cheapest months to fly
Lowest recently found return fare in each month. Tap a month to see that month's calendar.
Typical return fare: $157 – $183 Middle half of the lowest fares we saw each day in the last 90 days (8 days of data). Anything below the range is a good price.
Good priceHouston → Chicago
November 2026
Lowest fares for the best day
- Frontier AirlinesMon 23 Nov – Wed 25 Nov · Direct · 2h 54m $216
- Frontier AirlinesWed 25 Nov – Mon 30 Nov · 1 stop · 5h 32m $253
- Frontier AirlinesSun 1 Nov – Sun 22 Nov · 1 stop · 6h 03m $324
- Frontier AirlinesSun 1 Nov – Sun 29 Nov · 1 stop · 6h 03m $402
Airports in Chicago
- ORDO'Hare
- MDWMidway
Airports in Houston
- IAHGeorge Bush Intercontinental
- HOUHobby
Watch this route
FAQ
Questions about this route
Search the help center or send us a message. We reply by email.
Help center Contact us01What is the cheapest month to fly from Houston to Chicago?
Based on recently found fares, October 2026 has the lowest price we know of, from $137. Prices change often, so check the calendar for current fares.
02Which airports serve Chicago?
Chicago is served by O'Hare (ORD), Midway (MDW). Searching the city code compares all of them at once.
03Are the prices on this page final?
No. They are recently found fares. When you open a deal, the partner shows the live price, including taxes and fees, before you pay.
04How can I get an alert when flights to Chicago get cheaper?
Use the price alert on this page. Choose your dates or a whole month and we will email you when the fare drops.