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Cheap flights from Colorado to Chicago from $44

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Colorado to Chicago departing on 9/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
Frontier Logo
4:48 pm - 6:26 pmMDW-DEN
2h 38mnonstop
$97Frontier
Find Deal
Mon, Sep 8 - Mon, Sep 15
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
Frontier Logo
6:24 pm - 8:08 pmMDW-DEN
2h 44mnonstop
$107Frontier
Find Deal
Mon, Oct 6 - Fri, Oct 10
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
Frontier Logo
4:48 pm - 6:26 pmMDW-DEN
2h 38mnonstop
$113Frontier
Find Deal
Mon, Sep 22 - Fri, Sep 26
Frontier Logo
9:12 pm - 12:36 amDEN-MDW
2h 24mnonstop
Frontier Logo
6:24 pm - 8:08 pmMDW-DEN
2h 44mnonstop
$115Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Southwest Logo
10:25 am - 1:45 pmDEN-MDW
2h 20mnonstop
Southwest Logo
6:00 am - 7:35 amMDW-DEN
2h 35mnonstop
$137Southwest
Find Deal
Tue, Sep 9 - Wed, Sep 10
Southwest Logo
1:55 pm - 5:15 pmCOS-MDW
2h 20mnonstop
Southwest Logo
4:00 pm - 5:35 pmMDW-COS
2h 35mnonstop
$137Southwest
Find Deal
Wed, Oct 22 - Tue, Oct 28
Southwest Logo
10:25 am - 1:45 pmDEN-MDW
2h 20mnonstop
Southwest Logo
7:10 am - 8:45 amMDW-DEN
2h 35mnonstop
$147Southwest
Find Deal
Wed, Sep 3 - Mon, Sep 8
Delta Logo
6:00 am - 6:35 pmCOS-MDW
11h 35m2 stops
Delta Logo
9:35 am - 8:39 pmMDW-COS
12h 04m2 stops
$253Delta
Find Deal
Sat, Sep 13 - Tue, Sep 16
Delta Logo
5:55 pm - 9:48 amCOS-MDW
14h 53m2 stops
Delta Logo
6:00 am - 12:11 pmMDW-COS
7h 11m1 stop
$289Delta
Find Deal
Fri, Oct 3 - Mon, Oct 6
Delta Logo
1:10 pm - 9:26 pmCOS-MDW
7h 16m1 stop
Delta Logo
6:00 am - 12:12 pmMDW-COS
7h 12m1 stop
$319Delta
Find Deal
Thu, Sep 4 - Mon, Sep 8

Frontier flights from Colorado to Chicago Midway Airport

Our best Frontier deals on Colorado to Chicago Midway Airport flight tickets
Frontier
Sep 8
DEN12:28 pmDenver Intl
2h 25m
MDW3:53 pmChicago Midway
Sep 15
MDW4:48 pmChicago Midway
2h 38m
DEN6:26 pmDenver Intl
$97
Find similar
Frontier
Oct 6
DEN12:28 pmDenver Intl
2h 25m
MDW3:53 pmChicago Midway
Oct 10
MDW6:24 pmChicago Midway
2h 44m
DEN8:08 pmDenver Intl
$107
Find similar
Frontier
Sep 22
DEN12:28 pmDenver Intl
2h 25m
MDW3:53 pmChicago Midway
Sep 26
MDW4:48 pmChicago Midway
2h 38m
DEN6:26 pmDenver Intl
$113
Find similar

Delta flights from Colorado to Chicago Midway Airport

Our best Delta deals on Colorado to Chicago Midway Airport flight tickets
Delta
Sep 13
COS6:00 amColorado Springs
11h 35m
2 stops
MDW6:35 pmChicago Midway
Sep 16
MDW9:35 amChicago Midway
12h 04m
2 stops
COS8:39 pmColorado Springs
$253
Find similar
Delta
Oct 3
COS5:55 pmColorado Springs
14h 53m
2 stops
MDW9:48 amChicago Midway
Oct 6
MDW6:00 amChicago Midway
7h 11m
1 stop
COS12:11 pmColorado Springs
$289
Find similar
Delta
Sep 4
COS1:10 pmColorado Springs
7h 16m
1 stop
MDW9:26 pmChicago Midway
Sep 8
MDW6:00 amChicago Midway
7h 12m
1 stop
COS12:12 pmColorado Springs
$319
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Colorado to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Colorado to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 9/8

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Mon 9/15

4:48 pm-6:26 pm

Nonstop2h 38m

$97

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 10/6

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Fri 10/10

6:24 pm-8:08 pm

Nonstop2h 44m

$107

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 9/22

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Fri 9/26

4:48 pm-6:26 pm

Nonstop2h 38m

$113

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 10/16

9:12 pm-12:36 am

Nonstop2h 24m

Chicago Midway

Mon 10/20

6:24 pm-8:08 pm

Nonstop2h 44m

$115

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 9/9

10:25 am-1:45 pm

Nonstop2h 20m

Chicago Midway

Wed 9/10

6:00 am-7:35 am

Nonstop2h 35m

$137

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/22

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

Tue 10/28

4:00 pm-5:35 pm

Nonstop2h 35m

$137

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 9/3

10:25 am-1:45 pm

Nonstop2h 20m

Chicago Midway

Mon 9/8

7:10 am-8:45 am

Nonstop2h 35m

$147

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 9/13

6:00 am-6:35 pm

2 stops11h 35m

Chicago Midway

Tue 9/16

9:35 am-8:39 pm

2 stops12h 04m

$253

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 10/3

5:55 pm-9:48 am

2 stops14h 53m

Chicago Midway

Mon 10/6

6:00 am-12:11 pm

1 stop7h 11m

$289

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 9/4

1:10 pm-9:26 pm

1 stop7h 16m

Chicago Midway

Mon 9/8

6:00 am-12:12 pm

1 stop7h 12m

$319

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Colorado to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Colorado during the month September is also very affordable. Most momondo users find prices during this month for around $163.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Colorado. The lowest ticket price found for a Friday departure recently was $205. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Colorado because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $257.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Colorado in the evening is the least expensive time of day to depart. momondo users have found prices as low as $169 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $308. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Colorado to Chicago Midway flight route?

Fly from Denver Intl to Chicago Midway for the best Colorado - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Colorado when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $213 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Colorado for as low as $158 on momondo.

What cabin class options are available on Colorado to Chicago Midway flights?

There are 1 cabin classes available to choose from on Colorado to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Colorado to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Colorado to Chicago Midway Airport.

Cheap Colorado to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Colorado to Chicago Midway Airport

Best Price Found

$44

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Colorado in the past 72 hours is $44. The best round-trip flight deal from Colorado to Chicago Midway Airport found on momondo in the last 72 hours is $97.
The fastest flight from Colorado to Chicago Midway Airport takes 2h 15m
Direct flights go from Colorado to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Colorado to Chicago Midway Airport?

    Prices for flights from Colorado to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Colorado to Chicago Midway Airport?

  • How old do you have to be to fly from Colorado to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Colorado to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Colorado to Chicago Midway Airport?

Best airlines flying from Colorado to Chicago Midway Airport

Compare and see reviews for airlines that fly from Colorado to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $63Free CancellationRating
5.8
3,219 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
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Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Colorado to Chicago?

It is quick and easy to find Colorado to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Colorado to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Colorado on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Colorado to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Colorado to Chicago.

I’m not ready to book a flight from Colorado to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Colorado are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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