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Not ready to book? to track prices.Southwest flights from Colorado Springs to Chicago Midway Airport
Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Delta flights from Colorado Springs to Chicago Midway Airport
Our best Delta deals on Colorado Springs to Chicago Midway Airport flight tickets
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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
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Wed 10/28
12:40 pm-4:00 pm
Nonstop2h 20m
Chicago Midway
Mon 11/2
5:55 am-9:25 am
1 stop4h 30m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 10/27
12:40 pm-4:00 pm
Nonstop2h 20m
Chicago Midway
Mon 11/2
5:20 am-10:25 am
1 stop6h 05m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Sat 11/7
6:00 am-3:17 pm
1 stop8h 17m
Chicago Midway
Tue 11/10
1:05 pm-8:50 pm
1 stop8h 45m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Wed 11/4
1:31 pm-10:33 pm
1 stop8h 02m
Chicago Midway
Sat 11/7
6:04 am-12:21 pm
1 stop7h 17m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Sat 11/7
6:00 am-3:17 pm
1 stop8h 17m
Chicago Midway
Tue 11/10
6:00 am-12:26 pm
1 stop7h 26m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 11/10
1:31 pm-10:54 pm
1 stop8h 23m
Chicago Midway
Sat 11/14
6:00 am-12:26 pm
1 stop7h 26m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Sat 12/5
12:40 pm-7:50 pm
1 stop6h 10m
Chicago Midway
Thu 12/10
6:05 am-9:40 am
1 stop4h 35m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 11/10
1:40 pm-11:10 pm
1 stop8h 30m
Chicago Midway
Mon 11/16
5:20 am-1:00 pm
1 stop8h 40m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 11/24
1:25 pm-9:55 pm
1 stop7h 30m
Chicago Midway
Thu 11/26
6:00 am-12:50 pm
1 stop7h 50m
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Wed 10/28
12:40 pm-4:00 pm
Nonstop2h 20m
Chicago Midway
Sat 11/7
10:25 am-6:20 pm
2 stops8h 55m
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 April is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado Springs, with most prices found around $288. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Colorado Springs during the month January is also very affordable. Most momondo users find prices during this month for around $298.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Colorado Springs. The lowest ticket price found for a Saturday departure recently was $427. 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 $644.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Colorado Springs at noon is the least expensive time of day to depart. momondo users have found prices as low as $477 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $612. 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 Airport flights?
There is only 1 cabin class available to choose from on Colorado Springs to Chicago Midway Airport 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?
No. A direct flight is the cheapest option for a flight between Colorado Springs to Chicago Midway Airport.
When to book flights from Colorado Springs to Chicago Midway Airport
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
Frequently asked questions about flying from Colorado Springs to Chicago Midway Airport
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?
There is 1 operator available for flights from Colorado Springs Airport to Chicago Midway Airport as of October 2026.
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?
momondo data reveals that the most frequently booked plane model on the route from Colorado Springs to Chicago Midway Airport is Embraer 175 (Enhanced Winglets), representing 19.44% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 16.67%, Canadair (Bombardier) Regional Jet 700 at 15.28%, and Boeing 737 MAX 9 at 9.72%.
What is the most popular airline from Colorado Springs to Chicago Midway Airport?
Based on momondo bookings for flights between Colorado Springs and Chicago Midway Airport, the leading airline is Southwest, making up 100% of the total bookings.
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 | ||
|---|---|---|---|---|---|
| PriceFrom $243 | Free Cancellation | Rating 7.9 4,214 reviews |
Southwest Flights From Colorado Springs to Chicago Midway Airport
Southwest operates around 5 flights from Colorado Springs to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $424, but momondo users have found Southwest deals from Colorado Springs to Chicago Midway Airport from as low as $243 round-trip. Southwest has been scored 7.9/10 in 4,214 reviews.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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.