$98 Find Cheap Flights from Colorado to Chicago - Compare and Save

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Flight Deals

Cheap Flights from Colorado to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Colorado to Chicago

Sat, Nov 21 - Wed, Nov 25
Frontier Logo
9:26 pm - 12:53 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 27mnonstop
Frontier Logo
12:05 pm - 6:15 pmORD  Chicago O'Hare Intl-DEN Denver Intl
7h 10m1 stop Phoenix Sky Harbor Intl
$185Frontier
Sat, Nov 21 - Tue, Nov 24
Frontier Logo
9:26 pm - 12:53 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 27mnonstop
Frontier Logo
5:15 am - 11:56 amORD  Chicago O'Hare Intl-DEN Denver Intl
7h 41m1 stop Las Vegas Harry Reid Intl
$185Frontier
Sat, Dec 12 - Tue, Dec 15
American Airlines Logo
6:46 am - 10:30 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 44mnonstop
American Airlines Logo
10:40 pm - 12:30 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 50mnonstop
$199American Airlines
Tue, Dec 1 - Tue, Dec 8
American Airlines Logo
12:21 pm - 4:00 pmDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 39mnonstop
American Airlines Logo
9:45 am - 11:41 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 56mnonstop
$199American Airlines
Wed, Dec 2 - Sat, Dec 5
United Airlines Logo
6:00 pm - 9:34 pmDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 34mnonstop
United Airlines Logo
7:00 am - 8:46 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 46mnonstop
$199United Airlines
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
4:15 pm - 7:35 pmDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:05 am - 8:00 amMDW  Chicago Midway-DEN Denver Intl
2h 55mnonstop
$199Southwest
Tue, Dec 1 - Tue, Dec 8
Southwest Logo
7:05 am - 10:30 amDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
6:05 am - 8:00 amMDW  Chicago Midway-DEN Denver Intl
2h 55mnonstop
$199Southwest
Sat, Dec 5 - Wed, Dec 9
Delta Logo
6:10 am - 1:01 pmDEN  Denver Intl-MDW Chicago Midway
5h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:37 am - 3:15 pmMDW  Chicago Midway-DEN Denver Intl
6h 38m1 stop Detroit Metropolitan Wayne County
$219Delta
Tue, Dec 8 - Tue, Dec 8
Delta Logo
6:10 am - 1:01 pmDEN  Denver Intl-MDW Chicago Midway
5h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:30 pm - 11:49 pmMDW  Chicago Midway-DEN Denver Intl
7h 19m1 stop Minneapolis St Paul
$219Delta
Sat, Dec 12 - Thu, Jan 21
United Airlines Logo
6:00 pm - 9:34 pmDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 34mnonstop
United Airlines Logo
12:40 pm - 2:35 pmORD  Chicago O'Hare Intl-DEN Denver Intl
2h 55mnonstop
$221United Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$98
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 32% increase in price.
Flight from Denver to Chicago O'Hare Airport

Flights from Colorado to Chicago: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Colorado to Chicago 
JoanneFlew with United Airlines-Jun 2026
The runway to gate took a bit of time. So if you have a short layover pay for a seat up front .
AdamFlew with Southwest-Oct 2024
Arriving T5 at ORD on Southwest is often a LONG walk, with no moving walkways going out, to baggage claim / pickup.
BrianFlew with United Airlines-Jan 2024
Big airport. Make sure you have enough time between flights for rest, eating, etc…

FAQs for booking flights from Colorado to Chicago

  • How does KAYAK find such low prices on flights from Colorado to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Colorado to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Colorado to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Colorado is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Colorado to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Colorado with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Colorado to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Colorado up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago