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.

$101 CHEAP FLIGHTS from Colorado to Chicago

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Cheap Flights from Colorado to Chicago

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

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Colorado to Chicago

Fri, Oct 16 - Mon, Oct 19

11:48 pm - 10:58 amDEN Denver Intl-MDW Chicago Midway

10h 10m1 stop Atlanta Hartsfield-Jackson

12:03 pm - 10:33 pmMDW Chicago Midway-DEN Denver Intl

11h 30m1 stop Atlanta Hartsfield-Jackson

$164Frontier

Sat, Oct 10 - Tue, Oct 13

11:48 pm - 10:58 amDEN Denver Intl-MDW Chicago Midway

10h 10m1 stop Atlanta Hartsfield-Jackson

6:40 am - 2:00 pmMDW Chicago Midway-DEN Denver Intl

8h 20m1 stop Atlanta Hartsfield-Jackson

$164Frontier

Sat, Oct 10 - Sat, Oct 17

5:35 pm - 8:55 pmDEN Denver Intl-MDW Chicago Midway

2h 20mnonstop

6:15 am - 7:55 amMDW Chicago Midway-DEN Denver Intl

2h 40mnonstop

$165Southwest

Tue, Oct 20 - Mon, Oct 26

7:50 pm - 11:10 pmDEN Denver Intl-MDW Chicago Midway

2h 20mnonstop

6:25 pm - 8:05 pmMDW Chicago Midway-DEN Denver Intl

2h 40mnonstop

$165Southwest

Thu, Nov 12 - Mon, Nov 16

8:05 am - 11:45 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 40mnonstop

10:35 pm - 12:26 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 51mnonstop

$165American Airlines

Wed, Sep 23 - Thu, Sep 24

8:18 am - 11:59 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

10:30 pm - 12:17 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 47mnonstop

$165American Airlines

Wed, Sep 2 - Sat, Sep 5

5:48 pm - 9:29 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

2:42 pm - 4:34 pmORD Chicago O'Hare Intl-DEN Denver Intl

2h 52mnonstop

$165United Airlines

Wed, Sep 2 - Sat, Sep 5

5:48 pm - 9:29 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

7:00 am - 8:52 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 52mnonstop

$165United Airlines

Fri, Oct 30 - Sun, Nov 1

6:25 am - 10:01 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 36mnonstop

6:08 pm - 11:46 pmORD Chicago O'Hare Intl-DEN Denver Intl

6h 38m1 stop Minneapolis St Paul

$169Multiple Airlines

Sun, Oct 11 - Fri, Oct 30

10:38 am - 4:44 pmDEN Denver Intl-ORD Chicago O'Hare Intl

5h 06m1 stop Minneapolis St Paul

10:40 pm - 12:29 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 49mnonstop

$170Multiple Airlines

Recent last minute flight deals from Colorado to Chicago

Sat, Aug 15 - Wed, Sep 23

5:05 pm - 8:52 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

6:30 am - 8:15 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 45mnonstop

$174Frontier

Sat, Aug 15 - Wed, Sep 23

5:05 pm - 8:52 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

1:21 pm - 6:33 pmORD Chicago O'Hare Intl-DEN Denver Intl

30h 12m1 stop Las Vegas Harry Reid Intl

$210Frontier

Sat, Aug 15 - Wed, Sep 23

7:15 am - 10:35 amDEN Denver Intl-MDW Chicago Midway

2h 20mnonstop

8:50 pm - 10:30 pmMDW Chicago Midway-DEN Denver Intl

2h 40mnonstop

$311Southwest

Sat, Aug 15 - Wed, Sep 23

11:15 am - 4:55 pmDEN Denver Intl-MDW Chicago Midway

4h 40m1 stop Detroit Metropolitan Wayne County

8:50 pm - 10:30 pmMDW Chicago Midway-DEN Denver Intl

2h 40mnonstop

$317Southwest

Sat, Aug 15 - Wed, Sep 16

12:36 pm - 4:29 pmCOS Colorado Springs-ORD Chicago O'Hare Intl

2h 53mnonstop

5:00 am - 9:22 amORD Chicago O'Hare Intl-COS Colorado Springs

5h 22m1 stop Dallas/Fort Worth

$360American Airlines

Sat, Aug 15 - Wed, Sep 16

5:30 am - 11:28 amCOS Colorado Springs-ORD Chicago O'Hare Intl

4h 58m1 stop Denver Intl

5:00 am - 8:40 amORD Chicago O'Hare Intl-COS Colorado Springs

4h 40m1 stop Denver Intl

$360United Airlines

Sat, Aug 15 - Wed, Sep 16

12:36 pm - 4:29 pmCOS Colorado Springs-ORD Chicago O'Hare Intl

2h 53mnonstop

10:55 am - 12:48 pmORD Chicago O'Hare Intl-COS Colorado Springs

2h 53mnonstop

$377American Airlines

Sat, Aug 15 - Thu, Aug 20

5:05 pm - 8:52 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

5:29 pm - 11:14 pmORD Chicago O'Hare Intl-DEN Denver Intl

6h 45m1 stop Minneapolis St Paul

$385Multiple Airlines

Fri, Aug 14 - Thu, Aug 20

5:05 pm - 8:52 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

5:29 pm - 11:14 pmORD Chicago O'Hare Intl-DEN Denver Intl

6h 45m1 stop Minneapolis St Paul

$388Multiple Airlines

Tue, Aug 18 - Mon, Aug 24

2:50 pm - 6:32 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

5:55 am - 7:34 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 39mnonstop

$437United Airlines

Recent direct flight deals from Colorado to Chicago

Thu, Nov 12 - Mon, Nov 16

8:05 am - 11:45 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 40mnonstop

10:35 pm - 12:26 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 51mnonstop

$165American Airlines

Wed, Sep 23 - Thu, Sep 24

8:18 am - 11:59 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

10:30 pm - 12:17 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 47mnonstop

$165American Airlines

Wed, Sep 2 - Sat, Sep 5

5:48 pm - 9:29 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

2:42 pm - 4:34 pmORD Chicago O'Hare Intl-DEN Denver Intl

2h 52mnonstop

$165United Airlines

Wed, Sep 2 - Sat, Sep 5

5:48 pm - 9:29 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

7:00 am - 8:52 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 52mnonstop

$165United Airlines

Sat, Sep 26 - Sat, Oct 3

6:00 am - 9:20 amDEN Denver Intl-MDW Chicago Midway

2h 20mnonstop

7:25 pm - 9:05 pmMDW Chicago Midway-DEN Denver Intl

2h 40mnonstop

$165Southwest

Wed, Oct 14 - Tue, Oct 27

7:50 pm - 11:10 pmDEN Denver Intl-MDW Chicago Midway

2h 20mnonstop

6:05 am - 7:45 amMDW Chicago Midway-DEN Denver Intl

2h 40mnonstop

$165Southwest

Sat, Sep 26 - Mon, Sep 28

2:27 pm - 6:11 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 44mnonstop

6:41 pm - 8:35 pmORD Chicago O'Hare Intl-DEN Denver Intl

2h 54mnonstop

$165American Airlines

Tue, Oct 20 - Sat, Oct 24

4:40 pm - 8:22 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

7:50 pm - 9:44 pmORD Chicago O'Hare Intl-DEN Denver Intl

2h 54mnonstop

$165United Airlines

Fri, Nov 13 - Sun, Nov 15

6:25 am - 10:01 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 36mnonstop

10:40 pm - 12:29 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 49mnonstop

$166Frontier

Mon, Oct 12 - Thu, Oct 15

8:55 pm - 12:24 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 29mnonstop

6:30 am - 8:19 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 49mnonstop

$166Frontier

Useful Info

Low season	February
High season	July
Cheapest flight	$101

Best time to beat the crowds with an average 18% drop in price.

Most popular time to fly with an average 31% increase in price.

Flight from Colorado Springs to Chicago Midway Airport

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…

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.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Cabin class types available on flights to Colorado

First Class flights to Chicagofrom $252

Business Class flights to Chicagofrom $527

Premium Economy Class flights to Chicagofrom $995

Economy Class flights to Chicagofrom $160

$101 Find Cheap Flights from Colorado to Chicago - Compare and Save

Cheap Flights from Colorado to Chicago

Recent round-trip flight deals from Colorado to Chicago

Recent one-way flight deals from Colorado to Chicago

Recent last minute flight deals from Colorado to Chicago

Recent direct flight deals from Colorado to Chicago

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

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Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Colorado

Complete your trip to Chicago with a hotel stay or car rental

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