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.

$103 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

Tue, Oct 27 - Thu, Oct 29

10:56 am - 9:53 pmDEN Denver Intl-MDW Chicago Midway

9h 57m1 stop Atlanta Hartsfield-Jackson

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

11h 30m1 stop Atlanta Hartsfield-Jackson

$158Frontier

Sat, Oct 24 - Mon, Oct 26

6:05 am - 12:17 pmDEN Denver Intl-MDW Chicago Midway

5h 12m1 stop Dallas/Fort Worth

1:12 pm - 9:49 pmMDW Chicago Midway-DEN Denver Intl

9h 37m1 stop Dallas/Fort Worth

$158Frontier

Sat, Sep 19 - Tue, Sep 22

9:10 pm - 7:13 pmDEN Denver Intl-ORD Chicago O'Hare Intl

21h 03m1 stop Minneapolis St Paul

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

2h 45mnonstop

$177Multiple Airlines

Sat, Sep 19 - Mon, Sep 21

8:55 pm - 12:23 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 28mnonstop

11:47 am - 3:41 pmORD Chicago O'Hare Intl-DEN Denver Intl

4h 54m1 stop Minneapolis St Paul

$177Multiple Airlines

Sat, Sep 26 - Wed, Sep 30

5:20 pm - 8:50 pmDEN Denver Intl-MDW Chicago Midway

2h 30mnonstop

6:40 am - 8:10 amMDW Chicago Midway-DEN Denver Intl

2h 30mnonstop

$213Southwest

Mon, Sep 14 - Wed, Sep 16

8:25 pm - 11:50 pmDEN Denver Intl-MDW Chicago Midway

2h 25mnonstop

6:40 am - 8:10 amMDW Chicago Midway-DEN Denver Intl

2h 30mnonstop

$213Southwest

Wed, Sep 30 - Wed, Sep 30

12:29 pm - 4:10 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

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

2h 47mnonstop

$213American Airlines

Thu, Dec 31 - Thu, Jan 7

10:21 am - 1:58 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 37mnonstop

6:40 am - 8:33 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 53mnonstop

$213American Airlines

Thu, Oct 15 - Mon, Oct 19

7:10 pm - 10:46 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 36mnonstop

6:00 am - 7:39 amORD Chicago O'Hare Intl-DEN Denver Intl

2h 39mnonstop

$213United Airlines

Sat, Sep 12 - Mon, Sep 14

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

2h 42mnonstop

8:20 pm - 10:13 pmORD Chicago O'Hare Intl-DEN Denver Intl

2h 53mnonstop

$213United Airlines

Recent last minute flight deals from Colorado to Chicago

Sat, Aug 22 - Mon, Sep 21

9:55 am - 1:36 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

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

2h 45mnonstop

$178Frontier

Sat, Aug 22 - Mon, Sep 21

9:55 am - 1:36 pmDEN Denver Intl-ORD Chicago O'Hare Intl

2h 41mnonstop

8:55 pm - 12:46 pmORD Chicago O'Hare Intl-DEN Denver Intl

16h 51m1 stop Las Vegas Harry Reid Intl

$195Frontier

Sat, Aug 22 - Wed, Sep 9

11:04 am - 6:01 pmDEN Denver Intl-MDW Chicago Midway

5h 57m1 stop Minneapolis St Paul

7:13 pm - 11:35 pmMDW Chicago Midway-DEN Denver Intl

5h 22m1 stop Minneapolis St Paul

$335Delta

Tue, Aug 25 - Wed, Sep 9

6:05 am - 12:39 pmDEN Denver Intl-MDW Chicago Midway

5h 34m1 stop Detroit Metropolitan Wayne County

9:29 am - 1:57 pmMDW Chicago Midway-DEN Denver Intl

5h 28m1 stop Detroit Metropolitan Wayne County

$335Delta

Sat, Aug 22 - Mon, Sep 21

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

2h 20mnonstop

5:50 pm - 10:00 pmMDW Chicago Midway-DEN Denver Intl

5h 10m1 stop Lambert-St Louis

$366Southwest

Sat, Aug 22 - Mon, Sep 21

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

2h 20mnonstop

7:30 am - 9:00 amMDW Chicago Midway-DEN Denver Intl

2h 30mnonstop

$376Southwest

Tue, Aug 25 - Tue, Sep 8

12:37 pm - 4:30 pmCOS Colorado Springs-ORD Chicago O'Hare Intl

2h 53mnonstop

3:54 pm - 10:53 pmORD Chicago O'Hare Intl-COS Colorado Springs

7h 59m1 stop Dallas/Fort Worth

$392American Airlines

Tue, Aug 25 - Tue, Sep 8

10:12 am - 7:42 pmCOS Colorado Springs-ORD Chicago O'Hare Intl

8h 30m1 stop Dallas/Fort Worth

3:54 pm - 10:53 pmORD Chicago O'Hare Intl-COS Colorado Springs

7h 59m1 stop Dallas/Fort Worth

$402American Airlines

Sat, Aug 22 - Sat, Aug 22

6:00 am - 9:43 amDEN Denver Intl-ORD Chicago O'Hare Intl

2h 43mnonstop

5:51 pm - 7:45 pmORD Chicago O'Hare Intl-DEN Denver Intl

2h 54mnonstop

$437United Airlines

Tue, Aug 25 - Wed, Sep 2

7:55 am - 11:59 amCOS Colorado Springs-ORD Chicago O'Hare Intl

3h 04mnonstop

8:46 am - 10:33 amORD Chicago O'Hare Intl-COS Colorado Springs

2h 47mnonstop

$451United Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$103

Best time to beat the crowds with an average 19% drop in price.

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

Flight from Denver 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Return flight deals

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 $158

$103 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

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

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Colorado

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