People walking around Cloud Gate sculpture in Millennium Park with Chicago skyscrapers behind
56% below the usual fare
Exit Row · Boarding passSeat 14C

Cheap flights DenverChicago

From
DENDenver
To
CHIChicago
Travel
January 2027
Flight
Direct, one way

Fare from Denver

US$74

Usually about US$170

-56%vs the usual price

Get the dates and the link

Price seen 29 Oct 2026 · fares change fast and can sell out

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An aerial view of a large city next to a body of water
Ricky Beron / Unsplash
A view of a city at sunset from the top of a skyscraper
Raf Winterpacht / Unsplash

Why go

Chicago.

Skyscrapers, deep-dish pizza and live blues on the shore of Lake Michigan.

Best timeMay to September.

  • Big city
  • Food
  • Nightlife

Three things to do

  1. An architecture boat tour
  2. Deep-dish pizza and Chicago dogs
  3. Jazz and blues clubs
Distance
1,477 km
Flight
Direct
Trip
One way

Make it a trip.

Also boarding from Denver.

Every deal from Denver

Prices are the cheapest fare we found from Denver, in USD, for one adult, and can change when you click. Some links are affiliate links: they never change which deals we send or what you pay. How we make money.