Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Colorado Springs to Chicago from $70

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 Springs to Chicago departing on 9/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Colorado Springs to Chicago (COS-MDW)

Cheap round-trip flights

Southwest Logo
1:55 pm - 5:15 pmCOS-MDW
2h 20mnonstop
Southwest Logo
7:05 am - 11:40 amMDW-COS
5h 35m1 stop
$149Southwest
Find Deal
Wed, Oct 22 - Wed, Nov 5
Southwest Logo
3:30 pm - 10:50 pmCOS-MDW
6h 20m1 stop
Southwest Logo
2:45 pm - 4:10 pmMDW-COS
2h 25mnonstop
$161Southwest
Find Deal
Sat, Sep 27 - Tue, Sep 30
Southwest Logo
1:55 pm - 5:15 pmCOS-MDW
2h 20mnonstop
Southwest Logo
5:00 am - 11:40 amMDW-COS
7h 40m2 stops
$166Southwest
Find Deal
Wed, Oct 22 - Wed, Nov 5
Southwest Logo
9:45 am - 1:10 pmCOS-MDW
2h 25mnonstop
Southwest Logo
5:35 pm - 7:05 pmMDW-COS
2h 30mnonstop
$169Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 13
Southwest Logo
4:20 pm - 10:30 pmCOS-MDW
5h 10m1 stop
Southwest Logo
5:35 pm - 7:05 pmMDW-COS
2h 30mnonstop
$179Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 13
Southwest Logo
5:30 am - 5:05 pmCOS-MDW
10h 35m2 stops
Southwest Logo
5:25 am - 1:50 pmMDW-COS
9h 25m1 stop
$182Southwest
Find Deal
Wed, Oct 22 - Wed, Nov 5
Southwest Logo
3:30 pm - 10:50 pmCOS-MDW
6h 20m1 stop
Southwest Logo
3:50 pm - 10:00 pmMDW-COS
7h 10m1 stop
$183Southwest
Find Deal
Sat, Sep 27 - Tue, Sep 30
Southwest Logo
6:25 am - 2:45 pmCOS-MDW
7h 20m2 stops
Southwest Logo
5:35 pm - 7:05 pmMDW-COS
2h 30mnonstop
$184Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 13
Delta Logo
1:10 pm - 9:26 pmCOS-MDW
7h 16m1 stop
Delta Logo
1:08 pm - 8:41 pmMDW-COS
8h 33m2 stops
$222Delta
Find Deal
Fri, Sep 5 - Sat, Sep 6
Delta Logo
1:10 pm - 9:26 pmCOS-MDW
7h 16m1 stop
Delta Logo
1:08 pm - 8:41 pmMDW-COS
8h 33m2 stops
$252Delta
Find Deal
Fri, Sep 5 - Sat, Sep 6

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
Oct 22
COS1:55 pmColorado Springs
2h 20m
MDW5:15 pmChicago Midway
Nov 5
MDW7:05 amChicago Midway
5h 35m
1 stop
COS11:40 amColorado Springs
$149
Find similar
Southwest
Sep 27
COS3:30 pmColorado Springs
6h 20m
1 stop
MDW10:50 pmChicago Midway
Sep 30
MDW2:45 pmChicago Midway
2h 25m
COS4:10 pmColorado Springs
$161
Find similar
Southwest
Oct 22
COS1:55 pmColorado Springs
2h 20m
MDW5:15 pmChicago Midway
Nov 5
MDW5:00 amChicago Midway
7h 40m
2 stops
COS11:40 amColorado Springs
$166
Find similar

Delta flights from Colorado Springs to Chicago Midway Airport

Our best Delta deals on Colorado Springs to Chicago Midway Airport flight tickets
Delta
Sep 5
COS1:10 pmColorado Springs
7h 16m
1 stop
MDW9:26 pmChicago Midway
Sep 6
MDW1:08 pmChicago Midway
8h 33m
2 stops
COS8:41 pmColorado Springs
$222
Find similar
Delta
Sep 5
COS1:10 pmColorado Springs
7h 16m
1 stop
MDW9:26 pmChicago Midway
Sep 6
MDW1:08 pmChicago Midway
8h 33m
2 stops
COS8:41 pmColorado Springs
$252
Find similar
Delta
Sep 5
COS11:11 amColorado Springs
9h 15m
2 stops
MDW9:26 pmChicago Midway
Sep 6
MDW9:31 amChicago Midway
12h 10m
2 stops
COS8:41 pmColorado Springs
$257
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Colorado Springs 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 6, 2025.
Use the filters below to find and compare flights from Colorado Springs to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/22

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

Wed 11/5

7:05 am-11:40 am

1 stop5h 35m

$149

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 9/27

3:30 pm-10:50 pm

1 stop6h 20m

Chicago Midway

Tue 9/30

2:45 pm-4:10 pm

Nonstop2h 25m

$161

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/22

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

Wed 11/5

5:00 am-11:40 am

2 stops7h 40m

$166

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 9/4

9:45 am-1:10 pm

Nonstop2h 25m

Chicago Midway

Sat 9/13

5:35 pm-7:05 pm

Nonstop2h 30m

$169

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 9/4

4:20 pm-10:30 pm

1 stop5h 10m

Chicago Midway

Sat 9/13

5:35 pm-7:05 pm

Nonstop2h 30m

$179

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/22

5:30 am-5:05 pm

2 stops10h 35m

Chicago Midway

Wed 11/5

5:25 am-1:50 pm

1 stop9h 25m

$182

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 9/27

3:30 pm-10:50 pm

1 stop6h 20m

Chicago Midway

Tue 9/30

3:50 pm-10:00 pm

1 stop7h 10m

$183

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 9/4

6:25 am-2:45 pm

2 stops7h 20m

Chicago Midway

Sat 9/13

5:35 pm-7:05 pm

Nonstop2h 30m

$184

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 9/5

1:10 pm-9:26 pm

1 stop7h 16m

Chicago Midway

Sat 9/6

1:08 pm-8:41 pm

2 stops8h 33m

$222

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 9/5

1:10 pm-9:26 pm

1 stop7h 16m

Chicago Midway

Sat 9/6

1:08 pm-8:41 pm

2 stops8h 33m

$252

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Colorado Springs 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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado Springs, with most prices found around $281. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Colorado Springs during the month January is also very affordable. Most momondo users find prices during this month for around $291.

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 Springs. The lowest ticket price found for a Friday departure recently was $203. 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 Springs because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $255.

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

Flying to Chicago Midway Airport from Colorado Springs 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 $301. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Colorado Springs to Chicago Midway flight route?

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

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

There are 1 cabin classes available to choose from on Colorado Springs 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 Springs to Chicago Midway Airport flights?

You could potentially save up to 20% on your flight if you consider stops on a Colorado Springs to Chicago Midway Airport flight.

When to book flights from Colorado Springs to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Colorado Springs to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Colorado Springs to Chicago Midway Airport (COS to MDW) flight deals and tips

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

Best Price Found

$70

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Colorado Springs in the past 72 hours is $70. The best round-trip flight deal from Colorado Springs to Chicago Midway Airport found on momondo in the last 72 hours is $149.
The fastest flight from Colorado Springs to Chicago Midway Airport takes 2h 20m
Direct flights go from Colorado Springs to Chicago Midway Airport every day.
Search flight deals

  • How far is Colorado Springs to Chicago Midway by plane?

    The straight-line distance from Colorado Springs to Chicago Midway is 920.2 mi. Typically, this will take 2h 20m by plane in normal conditions.

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Colorado Springs Airport to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

  • What is the most popular airline from Colorado Springs to Chicago Midway Airport?

Best airlines flying from Colorado Springs to Chicago Midway Airport

Compare and see reviews for airlines that fly from Colorado Springs to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $281Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

  • Southwest Flights From Colorado Springs to Chicago Midway Airport

    Southwest operates around 2 flights from Colorado Springs to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $325, but momondo users have found Southwest deals from Colorado Springs to Chicago Midway Airport from as low as $281 round-trip. Southwest has been scored 8.0/10 in 4,244 reviews.

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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Colorado Springs.

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

momondo does allow users to show only those flights to Chicago from Colorado Springs which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Colorado Springs to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Colorado Springs to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 8/11
Mon 8/18
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago