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Cheap flights from Colorado to Chicago from $68

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 1/14. 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
12:05 am - 7:27 am
DEN
-
MDW
6h 22m1 stop
Frontier Logo
9:09 pm - 10:59 pm
MDW
-
DEN
2h 50mnonstop
$98Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
10:43 am - 2:05 pm
DEN
-
MDW
2h 22mnonstop
Frontier Logo
3:00 pm - 4:49 pm
MDW
-
DEN
2h 49mnonstop
$106Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
12:05 am - 7:27 am
DEN
-
MDW
6h 22m1 stop
Frontier Logo
9:15 am - 9:11 pm
MDW
-
DEN
12h 56m1 stop
$109Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
10:29 pm - 11:45 am
DEN
-
MDW
12h 16m1 stop
Frontier Logo
3:05 pm - 4:54 pm
MDW
-
DEN
2h 49mnonstop
$113Frontier
Wed, Jan 7 - Fri, Jan 9
Delta Logo
1:21 pm - 10:07 pm
COS
-
MDW
7h 46m1 stop
Delta Logo
6:25 am - 12:23 pm
MDW
-
COS
6h 58m1 stop
$263Delta
Sat, Jan 17 - Sat, Jan 24
Delta Logo
1:49 pm - 10:42 pm
HDN
-
MDW
7h 53m1 stop
Delta Logo
6:30 am - 12:53 pm
MDW
-
HDN
7h 23m1 stop
$274Delta
Thu, Mar 5 - Mon, Mar 9
Delta Logo
1:21 pm - 10:07 pm
COS
-
MDW
7h 46m1 stop
Delta Logo
6:45 am - 12:22 pm
MDW
-
COS
6h 37m1 stop
$279Delta
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
7:50 am - 5:20 pm
COS
-
MDW
8h 30m2 stops
Southwest Logo
10:05 am - 3:55 pm
MDW
-
COS
6h 50m1 stop
$284Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
11:15 am - 7:30 pm
MTJ
-
MDW
7h 15m1 stop
Southwest Logo
7:50 pm - 12:00 pm
MDW
-
MTJ
17h 10m2 stops
$285Southwest
Fri, Feb 20 - Tue, Feb 24
Southwest Logo
3:50 pm - 12:55 am
MTJ
-
MDW
8h 05m2 stops
Southwest Logo
7:50 pm - 12:00 pm
MDW
-
MTJ
17h 10m2 stops
$290Southwest
Fri, Feb 20 - Tue, Feb 24

Frontier flights from Colorado to Chicago Midway Airport

Our best Frontier deals on Colorado to Chicago Midway Airport flight tickets
Frontier
Jan 16
DEN12:05 amDenver Intl
6h 22m
1 stop
MDW7:27 amChicago Midway
Jan 19
MDW9:09 pmChicago Midway
2h 50m
DEN10:59 pmDenver Intl
$98
Find similar
Frontier
Jan 9
DEN10:43 amDenver Intl
2h 22m
MDW2:05 pmChicago Midway
Jan 12
MDW3:00 pmChicago Midway
2h 49m
DEN4:49 pmDenver Intl
$106
Find similar
Frontier
Jan 16
DEN12:05 amDenver Intl
6h 22m
1 stop
MDW7:27 amChicago Midway
Jan 19
MDW9:15 amChicago Midway
12h 56m
1 stop
DEN9:11 pmDenver Intl
$109
Find similar

Southwest flights from Colorado to Chicago Midway Airport

Our best Southwest deals on Colorado to Chicago Midway Airport flight tickets
Southwest
Jan 13
DEN9:45 amDenver Intl
2h 25m
MDW1:10 pmChicago Midway
Jan 14
MDW2:10 pmChicago Midway
2h 40m
DEN3:50 pmDenver Intl
$173
Find similar
Southwest
Jan 13
DEN10:15 amDenver Intl
5h 10m
1 stop
MDW4:25 pmChicago Midway
Jan 20
MDW7:55 pmChicago Midway
2h 45m
DEN9:40 pmDenver Intl
$175
Find similar
Southwest
Jan 13
DEN4:35 pmDenver Intl
2h 20m
MDW7:55 pmChicago Midway
Jan 14
MDW1:15 pmChicago Midway
4h 05m
1 stop
DEN4:20 pmDenver Intl
$183
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 December 18, 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

Fri 1/16

12:05 am-7:27 am

1 stop6h 22m

Chicago Midway

Mon 1/19

9:09 pm-10:59 pm

Nonstop2h 50m

$98

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Mon 1/12

3:00 pm-4:49 pm

Nonstop2h 49m

$106

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/16

12:05 am-7:27 am

1 stop6h 22m

Chicago Midway

Mon 1/19

9:15 am-9:11 pm

1 stop12h 56m

$109

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 1/7

10:29 pm-11:45 am

1 stop12h 16m

Chicago Midway

Fri 1/9

3:05 pm-4:54 pm

Nonstop2h 49m

$113

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 1/17

1:21 pm-10:07 pm

1 stop7h 46m

Chicago Midway

Sat 1/24

6:25 am-12:23 pm

1 stop6h 58m

$263

HaydenChicago

HDN - MDW

HDNMDW

Hayden Yampa Valley

Thu 3/5

1:49 pm-10:42 pm

1 stop7h 53m

Chicago Midway

Mon 3/9

6:30 am-12:53 pm

1 stop7h 23m

$274

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 1/15

1:21 pm-10:07 pm

1 stop7h 46m

Chicago Midway

Sun 1/18

6:45 am-12:22 pm

1 stop6h 37m

$279

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 1/15

7:50 am-5:20 pm

2 stops8h 30m

Chicago Midway

Sun 1/18

10:05 am-3:55 pm

1 stop6h 50m

$284

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 2/20

11:15 am-7:30 pm

1 stop7h 15m

Chicago Midway

Tue 2/24

7:50 pm-12:00 pm

2 stops17h 10m

$285

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 2/20

3:50 pm-12:55 am

2 stops8h 05m

Chicago Midway

Tue 2/24

7:50 pm-12:00 pm

2 stops17h 10m

$290

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 $177.

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 $226. 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, Saturday 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 $303.

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 $179 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $331. 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 $220 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 $179 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

$161

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 $161. The best round-trip flight deal from Colorado to Chicago Midway Airport found on momondo in the last 72 hours is $155.
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 $68Free CancellationRating
5.8
3,080 reviews
Search Frontier flights
SouthwestPriceFrom $157Free CancellationRating
7.9
4,252 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
Valparaiso
Schererville
Crown Point
Munster
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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