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Cheap flights from Dallas to Chicago

Recently found return fares from $111, with November 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.

$143 Oct2026 $111 Nov2026 $142 Dec2026

Dallas → Chicago

November 2026

Mon Tue Wed Thu Fri Sat Sun 1 2 3 4 $122 5 $118 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 $111 23 24 25 26 27 28 29 30
LowerHigherLowest this month

Lowest fares for the best day

  • Frontier AirlinesSun 22 Nov – Sun 29 Nov · Direct · 2h 32m $243
  • Frontier AirlinesSun 22 Nov – Sun 29 Nov · 1 stop · 6h 52m $261
  • Frontier AirlinesSun 22 Nov – Sun 29 Nov · 1 stop · 5h 26m $267
  • Southwest AirlinesSun 22 Nov – Sun 29 Nov · Direct · 2h 15m $310
  • American AirlinesSun 22 Nov – Sun 29 Nov · Direct · 2h 44m $314
See all flights for these dates

Airports in Chicago

  • ORDO'Hare
  • MDWMidway

Airports in Dallas

  • DFWDallas/Fort Worth
  • DALLove Field

Watch this route

DFW
CHI

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More trips from Dallas

All flights from Dallas Chicago to Dallas flights
Denverfrom $73 Las Vegasfrom $79 FLLfrom $97 CLEfrom $126 RDUfrom $134 Miamifrom $138 Orlandofrom $144 Atlantafrom $157

FAQ

Questions about this route

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Help center Contact us
01What is the cheapest month to fly from Dallas to Chicago?

Based on recently found fares, November 2026 has the lowest price we know of, from $111. 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.