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Cheap flights from Colorado to Chicago from $95

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 6/10. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:58 am - 10:11 pm
DEN
-
MDW
11h 13m
1 stop
Frontier Logo
12:11 pm - 10:05 pm
MDW
-
DEN
10h 54m
1 stop
$190Frontier
Wed, Jul 1 - Tue, Jul 7
Frontier Logo
9:58 am - 10:08 pm
DEN
-
MDW
11h 10m
1 stop
Frontier Logo
12:11 pm - 10:05 pm
MDW
-
DEN
10h 54m
1 stop
$200Frontier
Wed, Aug 12 - Sat, Aug 15
Frontier Logo
9:58 am - 10:08 pm
DEN
-
MDW
11h 10m
1 stop
Frontier Logo
12:11 pm - 10:05 pm
MDW
-
DEN
10h 54m
1 stop
$204Frontier
Wed, Aug 12 - Sat, Aug 15
Frontier Logo
11:54 pm - 11:12 am
DEN
-
MDW
10h 18m
1 stop
Frontier Logo
6:00 am - 2:04 pm
MDW
-
DEN
9h 04m
1 stop
$205Frontier
Wed, May 27 - Tue, Jun 2
Southwest Logo
6:15 am - 9:40 am
DEN
-
MDW
2h 25mnonstop
Southwest Logo
5:30 am - 7:05 am
MDW
-
DEN
2h 35mnonstop
$217Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
10:15 am - 11:45 am
MDW
-
COS
2h 30mnonstop
$351Southwest
Tue, Aug 25 - Sun, Aug 30
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
10:15 am - 11:45 am
MDW
-
COS
2h 30mnonstop
$357Southwest
Tue, Aug 25 - Sun, Aug 30
Delta Logo
11:27 am - 6:01 pm
COS
-
MDW
5h 34m
1 stop
Delta Logo
6:05 am - 12:15 pm
MDW
-
COS
7h 10m
1 stop
$371Delta
Tue, Aug 25 - Sat, Aug 29
Delta Logo
1:40 pm - 10:17 pm
COS
-
MDW
7h 37m
1 stop
Delta Logo
1:49 pm - 10:41 pm
MDW
-
COS
9h 52m
2 stops
$376Delta
Thu, Jul 2 - Tue, Jul 7
Delta Logo
6:00 am - 6:01 pm
COS
-
MDW
11h 01m
2 stops
Delta Logo
9:24 am - 5:36 pm
MDW
-
COS
9h 12m
2 stops
$382Delta
Tue, Aug 25 - Sat, Aug 29

Delta flights from Colorado to Chicago Midway Airport

Our best Delta deals on Colorado to Chicago Midway Airport flight tickets
Delta
Jul 1
DEN6:00 amDenver Intl
6h 09m
1 stop
MDW1:09 pmChicago Midway
Jul 8
MDW7:06 pmChicago Midway
5h 21m
1 stop
DEN11:27 pmDenver Intl
$237
Delta
Jun 6
DEN6:05 amDenver Intl
5h 37m
1 stop
MDW12:42 pmChicago Midway
Jun 13
MDW9:17 amChicago Midway
5h 39m
1 stop
DEN1:56 pmDenver Intl
$257
Delta
Jul 1
DEN6:00 amDenver Intl
6h 09m
1 stop
MDW1:09 pmChicago Midway
Jul 10
MDW7:06 pmChicago Midway
5h 21m
1 stop
DEN11:27 pmDenver Intl
$261

Frontier flights from Colorado to Chicago Midway Airport

Our best Frontier deals on Colorado to Chicago Midway Airport flight tickets
Frontier
Jul 1
DEN9:58 amDenver Intl
11h 13m
1 stop
MDW10:11 pmChicago Midway
Jul 7
MDW12:11 pmChicago Midway
10h 54m
1 stop
DEN10:05 pmDenver Intl
$190
Frontier
Jun 6
DEN11:54 pmDenver Intl
10h 18m
1 stop
MDW11:12 amChicago Midway
Jun 9
MDW12:27 pmChicago Midway
10h 49m
1 stop
DEN10:16 pmDenver Intl
$200
Frontier
Aug 12
DEN9:58 amDenver Intl
11h 10m
1 stop
MDW10:08 pmChicago Midway
Aug 15
MDW12:11 pmChicago Midway
10h 54m
1 stop
DEN10:05 pmDenver Intl
$204

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 May 14, 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

Cheapest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 7/1

9:58 am-10:11 pm

1 stop11h 13m

Chicago Midway

Tue 7/7

12:11 pm-10:05 pm

1 stop10h 54m

$190

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 8/12

9:58 am-10:08 pm

1 stop11h 10m

Chicago Midway

Sat 8/15

12:11 pm-10:05 pm

1 stop10h 54m

$200

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 8/12

9:58 am-10:08 pm

1 stop11h 10m

Chicago Midway

Sat 8/15

12:11 pm-10:05 pm

1 stop10h 54m

$204

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 5/27

11:54 pm-11:12 am

1 stop10h 18m

Chicago Midway

Tue 6/2

6:00 am-2:04 pm

1 stop9h 04m

$205

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 6/9

6:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Tue 6/16

5:30 am-7:05 am

Nonstop2h 35m

$217
Quickest round-trip

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

1:15 pm-4:35 pm

Nonstop2h 20m

Chicago Midway

Sun 8/30

10:15 am-11:45 am

Nonstop2h 30m

$351

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

6:15 am-12:00 pm

1 stop4h 45m

Chicago Midway

Sun 8/30

10:15 am-11:45 am

Nonstop2h 30m

$357

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

11:27 am-6:01 pm

1 stop5h 34m

Chicago Midway

Sat 8/29

6:05 am-12:15 pm

1 stop7h 10m

$371

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 7/2

1:40 pm-10:17 pm

1 stop7h 37m

Chicago Midway

Tue 7/7

1:49 pm-10:41 pm

2 stops9h 52m

$376

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

6:00 am-6:01 pm

2 stops11h 01m

Chicago Midway

Sat 8/29

9:24 am-5:36 pm

2 stops9h 12m

$382

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 April is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado, with most prices found around $42. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Colorado during the month June is also very affordable. Most momondo users find prices during this month for around $57.

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 $245. 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 $367.

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 $247 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $364. 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 from Colorado 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 $270 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 $192 on momondo.

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

You could potentially save up to 10% on your flight if you consider stops on a Colorado to Chicago Midway Airport flight.

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

$162

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 $162. The best round-trip flight deal from Colorado to Chicago Midway Airport found on momondo in the last 72 hours is $306.
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

Frequently asked questions about flying from Colorado to Chicago Midway Airport

  • 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 $107Free CancellationRating
5.6
2,953 reviews
Search Frontier flights
SouthwestPriceFrom $163Free CancellationRating
8.0
4,299 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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