$103 Find Cheap Flights from Colorado to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Colorado to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Colorado to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Colorado to Chicago

Mon, Aug 10 - Sun, Aug 23
Frontier Logo
5:05 pm - 8:52 pm
DEN
-
ORD
2h 47mnonstop
Frontier Logo
2:41 pm - 4:45 pm
ORD
-
DEN
3h 04mnonstop
$181Frontier
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
12:25 pm - 8:15 pm
DEN
-
MDW
6h 50m
1 stop
Southwest Logo
8:15 pm - 9:50 pm
MDW
-
DEN
2h 35mnonstop
$181Southwest
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:05 am - 12:39 pm
DEN
-
MDW
5h 34m
1 stop
Delta Logo
7:13 pm - 11:35 pm
MDW
-
DEN
5h 22m
1 stop
$197Delta
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
12:37 pm - 4:30 pm
COS
-
ORD
2h 53mnonstop
American Airlines Logo
6:49 pm - 8:39 pm
ORD
-
COS
2h 50mnonstop
$215American Airlines
Sat, Sep 12 - Tue, Sep 15
American Airlines Logo
5:06 am - 8:56 am
COS
-
ORD
2h 50mnonstop
American Airlines Logo
10:55 am - 12:48 pm
ORD
-
COS
2h 53mnonstop
$217American Airlines
Sat, Sep 12 - Tue, Sep 15
United Airlines Logo
5:30 am - 12:19 pm
COS
-
ORD
5h 49m
1 stop
United Airlines Logo
8:55 am - 10:47 am
ORD
-
COS
2h 52mnonstop
$225United Airlines
Sat, Sep 12 - Wed, Sep 16
Delta Logo
1:25 pm - 10:45 pm
COS
-
MDW
8h 20m
1 stop
Delta Logo
1:00 pm - 7:56 pm
MDW
-
COS
7h 56m
1 stop
$235Delta
Fri, Aug 7 - Wed, Aug 19
United Airlines Logo
12:11 pm - 3:56 pm
COS
-
ORD
2h 45mnonstop
United Airlines Logo
8:46 am - 10:33 am
ORD
-
COS
2h 47mnonstop
$246United Airlines
Thu, Aug 20 - Sun, Aug 23
Multiple Airlines Logo
8:31 am - 3:09 pm
DEN
-
RFD
5h 38m
1 stop
Multiple Airlines Logo
9:35 pm - 3:48 am
RFD
-
DEN
7h 13m
1 stop
$268Multiple Airlines
Thu, Aug 6 - Thu, Aug 13
Multiple Airlines Logo
10:36 pm - 8:34 pm
DEN
-
RFD
20h 58m
1 stop
Multiple Airlines Logo
9:01 am - 2:31 pm
RFD
-
DEN
6h 30m
1 stop
$279Multiple Airlines
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Good to know

Low seasonFebruary
Cheapest flight$103
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 17% 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 
Learn how KAYAK collects reviews and tips from users.
JoanneFlew with United Airlines
DEN
-
ORD
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
DEN
-
ORD
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
DEN
-
ORD
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
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Colorado

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $854
Business Class flights to Chicagofrom $641
Premium Economy Class flights to Chicagofrom $505
Economy Class flights to Chicagofrom $154