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Cheap flights from Colorado to Chicago from $84

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 3/7. 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

Enter your travel dates to find the best prices.
Frontier Logo
10:20 am - 8:21 pm
DEN
-
MDW
9h 01m
1 stop
Frontier Logo
11:25 am - 6:36 pm
MDW
-
DEN
8h 11m
1 stop
$133Frontier
Sat, Mar 7 - Wed, Mar 11
Frontier Logo
12:59 am - 7:07 pm
DEN
-
MDW
17h 08m
1 stop
Frontier Logo
6:05 am - 11:04 pm
MDW
-
DEN
17h 59m
1 stop
$139Frontier
Tue, Mar 3 - Wed, Mar 11
Frontier Logo
12:59 am - 7:07 pm
DEN
-
MDW
17h 08m
1 stop
Frontier Logo
9:16 pm - 6:02 am
MDW
-
DEN
9h 46m
1 stop
$144Frontier
Mon, Mar 2 - Sat, Mar 7
Frontier Logo
2:15 pm - 4:16 pm
DEN
-
MDW
25h 01m
1 stop
Frontier Logo
7:15 am - 9:35 pm
MDW
-
DEN
15h 20m
1 stop
$151Frontier
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
2:19 pm - 4:16 pm
DEN
-
MDW
24h 57m
2 stops
Multiple Airlines Logo
11:25 am - 6:36 pm
MDW
-
DEN
8h 11m
1 stop
$152Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
Frontier Logo
12:42 pm - 9:12 pm
DEN
-
MDW
7h 30m
1 stop
Frontier Logo
2:19 pm - 9:41 pm
MDW
-
DEN
8h 22m
1 stop
$153Frontier
Thu, Feb 26 - Mon, Mar 2
Southwest Logo
8:45 pm - 5:20 am
COS
-
MDW
7h 35m
1 stop
Southwest Logo
5:55 am - 9:25 am
MDW
-
COS
4h 30m
1 stop
$246Southwest
Mon, Mar 30 - Sat, Apr 4
Southwest Logo
6:10 pm - 11:10 pm
COS
-
MDW
4h 00m
1 stop
Southwest Logo
7:45 am - 2:30 pm
MDW
-
COS
7h 45m
1 stop
$249Southwest
Fri, Feb 27 - Tue, Mar 3
Delta Logo
1:13 pm - 10:28 pm
COS
-
MDW
8h 15m
1 stop
Delta Logo
6:00 am - 12:17 pm
MDW
-
COS
7h 17m
1 stop
$266Delta
Thu, Apr 23 - Mon, Apr 27
Delta Logo
3:10 pm - 10:31 pm
EGE
-
MDW
6h 21m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$374Delta
Wed, Mar 4 - Wed, Mar 11

Southwest flights from Colorado to Chicago Midway Airport

Our best Southwest deals on Colorado to Chicago Midway Airport flight tickets
Southwest
Mar 7
DEN5:55 amDenver Intl
2h 25m
MDW9:20 amChicago Midway
Mar 14
MDW5:55 amChicago Midway
2h 45m
DEN7:40 amDenver Intl
$162
Southwest
Mar 7
DEN8:10 amDenver Intl
2h 25m
MDW11:35 amChicago Midway
Mar 14
MDW5:55 amChicago Midway
2h 45m
DEN7:40 amDenver Intl
$174
Southwest
Apr 8
DEN5:55 pmDenver Intl
2h 35m
MDW9:30 pmChicago Midway
Apr 11
MDW5:30 pmChicago Midway
2h 40m
DEN7:10 pmDenver Intl
$188

Frontier flights from Colorado to Chicago Midway Airport

Our best Frontier deals on Colorado to Chicago Midway Airport flight tickets
Frontier
Mar 7
DEN10:20 amDenver Intl
9h 01m
1 stop
MDW8:21 pmChicago Midway
Mar 11
MDW11:25 amChicago Midway
8h 11m
1 stop
DEN6:36 pmDenver Intl
$133
Frontier
Mar 3
DEN12:59 amDenver Intl
17h 08m
1 stop
MDW7:07 pmChicago Midway
Mar 11
MDW6:05 amChicago Midway
17h 59m
1 stop
DEN11:04 pmDenver Intl
$139
Frontier
Mar 2
DEN12:59 amDenver Intl
17h 08m
1 stop
MDW7:07 pmChicago Midway
Mar 7
MDW9:16 pmChicago Midway
9h 46m
1 stop
DEN6:02 amDenver Intl
$144

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 February 7, 2026.
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

Sat 3/7

10:20 am-8:21 pm

1 stop9h 01m

Chicago Midway

Wed 3/11

11:25 am-6:36 pm

1 stop8h 11m

$133

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 3/3

12:59 am-7:07 pm

1 stop17h 08m

Chicago Midway

Wed 3/11

6:05 am-11:04 pm

1 stop17h 59m

$139

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 3/2

12:59 am-7:07 pm

1 stop17h 08m

Chicago Midway

Sat 3/7

9:16 pm-6:02 am

1 stop9h 46m

$144

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 2/25

2:15 pm-4:16 pm

1 stop25h 01m

Chicago Midway

Wed 3/4

7:15 am-9:35 pm

1 stop15h 20m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 3/4

2:19 pm-4:16 pm

2 stops24h 57m

Chicago Midway

Wed 3/11

11:25 am-6:36 pm

1 stop8h 11m

$152

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 2/26

12:42 pm-9:12 pm

1 stop7h 30m

Chicago Midway

Mon 3/2

2:19 pm-9:41 pm

1 stop8h 22m

$153

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 3/30

8:45 pm-5:20 am

1 stop7h 35m

Chicago Midway

Sat 4/4

5:55 am-9:25 am

1 stop4h 30m

$246

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 2/27

6:10 pm-11:10 pm

1 stop4h 00m

Chicago Midway

Tue 3/3

7:45 am-2:30 pm

1 stop7h 45m

$249

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/23

1:13 pm-10:28 pm

1 stop8h 15m

Chicago Midway

Mon 4/27

6:00 am-12:17 pm

1 stop7h 17m

$266

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 3/4

3:10 pm-10:31 pm

1 stop6h 21m

Chicago Midway

Wed 3/11

6:00 am-2:11 pm

1 stop9h 11m

$374

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 $141. 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 $177.

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

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Colorado. The lowest ticket price found for a Monday departure recently was $225. 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 $294.

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 $190 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $327. 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 $224 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 $187 on momondo.

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

There is only 1 cabin class 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

$168

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 $168. The best round-trip flight deal from Colorado to Chicago Midway Airport found on momondo in the last 72 hours is $228.
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 $78Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
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.

An easier way to manage your Chicago Midway Airport trip

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