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Cheap flights from Washington to Chicago

Recently found return fares from $88, 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.

$134 Oct2026 $88 Nov2026 $193 Apr2027 $193 Jun2027

Washington → Chicago

November 2026

Mon Tue Wed Thu Fri Sat Sun 1 $134 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 $97 17 18 19 $45 20 21 22 23 24 25 $114 26 27 28 29 $200 30 $129
LowerHigherLowest this month

Lowest fares for the best day

  • Frontier AirlinesWed 11 Nov – Mon 16 Nov · 1 stop · 4h 37m $108
  • Frontier AirlinesFri 20 Nov – Sun 22 Nov · Direct · 2h 28m $120
  • Frontier AirlinesWed 4 Nov – Sat 7 Nov · 1 stop · 4h 19m $233
  • Frontier AirlinesSun 1 Nov – Wed 4 Nov · 1 stop · 6h 36m $327
  • Frontier AirlinesSun 29 Nov – Sun 29 Nov · 1 stop · 4h 46m $412
See all flights for these dates

Airports in Chicago

  • ORDO'Hare
  • MDWMidway

Airports in Washington

  • IADDulles
  • DCAReagan National

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CHI

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More trips from Washington

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Orlandofrom $40 Atlantafrom $73 Dallasfrom $82 Bostonfrom $149 Los Angelesfrom $155 ONTfrom $169 Miamifrom $180 FLLfrom $198

FAQ

Questions about this route

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

Based on recently found fares, November 2026 has the lowest price we know of, from $88. 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.