·
Route

Washington, DC to Chicago: what the flight costs

By the VacayMatch editors · Updated

In the last 60 days we checked this route 21 times. The typical return was £305 per person and the lowest £267, taxes and fees included.

Per person
Lowest seen£267
Typical (median)£305
Price checks, 60 days21

Check live prices

Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn

Trips we picked on this route

Next weekend · from Washington, DCLowest in 30 daysWorth it, if

Chicago

16 – 18 Oct 2026 · 2 nights

  • $354 per person, $12 under the typical $366 on this route
  • Saturday mostly clear at 52°F, Sunday clear at 61°F
  • Sleep Inn Midway Airport: $369 for 2 nights, breakfast, free cancellation
The total, before you go

£899 for two · 2 nights · flights, hotel, taxes & fees

Flights £534 + hotel £366, taxes in · a checked bag each adds about £181

Frontier · with a stop · 7h 24m

The catch: The Frontier flight has one stop and takes 7h 24m, landing at 12:24 AM Saturday; a checked bag is about $240 for two and isn't in the total.

Worth it if you want a low-cost city weekend and don't mind a late arrival; skip it if you need a nonstop or a downtown hotel.

Stay from £139/nightThings to do
See the pick

Every fare we found in the last 30 days

CheckedTrip datesPer personAirlineStopsDurationSource
15 Oct 202623 – 25 Oct 2026£416UAnonstop2h 14mKiwi.com
14 Oct 202623 – 25 Oct 2026£412AAnonstop2h 22mKiwi.com
14 Oct 202616 – 18 Oct 2026£415UAnonstop2h 14mKiwi.com
14 Oct 202623 – 25 Oct 2026£358B6with a stop16h 11mKiwi.com
14 Oct 202623 – 25 Oct 2026£282Frontierwith a stop7h 24mGoogle Flights
14 Oct 202616 – 18 Oct 2026£267Frontierwith a stop7h 24mGoogle Flights
14 Oct 202623 – 25 Oct 2026£305F9with a stop7h 24mKiwi.com
14 Oct 202616 – 18 Oct 2026£415UAnonstop2h 14mKiwi.com
13 Oct 202623 – 25 Oct 2026£359B6with a stop16h 11mKiwi.com
13 Oct 202623 – 25 Oct 2026£267Frontierwith a stop7h 24mGoogle Flights
13 Oct 202623 – 25 Oct 2026£297F9with a stop7h 24mKiwi.com
13 Oct 202616 – 18 Oct 2026£415UAnonstop2h 14mKiwi.com
13 Oct 202623 – 25 Oct 2026£297F9with a stop7h 24mKiwi.com
12 Oct 202623 – 25 Oct 2026£267Frontierwith a stop7h 24mGoogle Flights
12 Oct 202616 – 18 Oct 2026£267Frontierwith a stop7h 24mGoogle Flights
12 Oct 202623 – 25 Oct 2026£285F9with a stop7h 24mKiwi.com
12 Oct 202616 – 18 Oct 2026£398UAnonstop2h 14mKiwi.com
11 Oct 202623 – 25 Oct 2026£267Frontierwith a stop7h 24mGoogle Flights
11 Oct 202616 – 18 Oct 2026£267Frontierwith a stop7h 24mGoogle Flights
11 Oct 202623 – 25 Oct 2026£315F9with a stop7h 24mKiwi.com
11 Oct 202616 – 18 Oct 2026£311F9with a stop7h 24mKiwi.com

About Chicago

Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.

Chicago from every city: when to go, where to stay, what to do

Questions about Washington, DC to Chicago

What does a return from Washington, DC to Chicago usually cost?

Over the last 60 days the typical price we found was £305 per person, taxes and fees included, across 21 checks; the lowest was £267.

When is the best time to fly from Washington, DC to Chicago?

Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake

Do I need a passport to fly from Washington, DC to Chicago?

No passport needed for travellers from the United States: a government photo ID is enough for Chicago.

Prices converted from US dollars at the rate of 15 Oct 2026.

All trips from Washington, DC · Chicago hub · Home