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Southwest flights from Chicago Midway Airport to Colorado Springs
Our best Southwest deals on Chicago Midway Airport to Colorado Springs flight tickets
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Use the filters below to find and compare flights from Chicago Midway Airport to Colorado Springs that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Tue 10/27
3:35 pm-5:10 pm
Nonstop2h 35m
Colorado Springs
Sat 10/31
9:30 am-4:45 pm
1 stop6h 15m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Tue 10/27
3:35 pm-5:10 pm
Nonstop2h 35m
Colorado Springs
Sat 10/31
9:30 am-6:45 pm
2 stops8h 15m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Sat 11/7
6:04 am-12:21 pm
1 stop7h 17m
Colorado Springs
Sat 11/14
6:00 am-3:12 pm
1 stop8h 12m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 2/18
6:00 am-12:58 pm
1 stop7h 58m
Colorado Springs
Sat 2/20
1:40 pm-10:10 pm
1 stop7h 30m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Mon 11/9
5:20 am-10:25 am
1 stop6h 05m
Colorado Springs
Thu 11/12
7:45 pm-5:45 am
1 stop9h 00m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 12/3
5:00 pm-10:00 pm
1 stop6h 00m
Colorado Springs
Sat 12/5
12:40 pm-7:50 pm
1 stop6h 10m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Sat 11/7
6:04 am-12:21 pm
1 stop7h 17m
Colorado Springs
Tue 11/10
1:31 pm-10:54 pm
1 stop8h 23m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Tue 10/27
6:05 am-9:45 am
1 stop4h 40m
Colorado Springs
Sat 10/31
8:45 am-4:45 pm
2 stops7h 00m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Mon 11/9
5:20 am-10:25 am
1 stop6h 05m
Colorado Springs
Thu 11/12
4:40 pm-1:10 am
2 stops7h 30m
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 12/3
7:05 am-2:25 pm
1 stop8h 20m
Colorado Springs
Sat 12/5
6:00 am-2:30 pm
2 stops7h 30m
See travel insights to Colorado Springs from
How to get the cheapest flight ticket from Chicago Midway Airport to Colorado Springs
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 Colorado Springs?
The month of April is another great option to travel to Colorado Springs, with average flight prices from Chicago Midway Airport averaging around $229.
What is the cheapest day to depart on your flight to Colorado Springs?
The cheapest day to depart from Chicago Midway Airport to Colorado Springs is on a Wednesday when prices can be found for as low as $348. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Colorado Springs for around $452.
What is the cheapest time of day to depart on your flight to Colorado Springs?
Flying to Colorado Springs from Chicago Midway Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $353 when looking at flights departing in the afternoon. Flights to Colorado Springs are more costly in the evening, with an average ticket price of $489. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago Midway to Colorado Springs flight route?
Fly from Chicago Midway to Colorado Springs for the best Chicago Midway - Colorado Springs flight prices
What cabin class options are available on Chicago Midway Airport to Colorado Springs flights?
There is only 1 cabin class available to choose from on Chicago Midway Airport to Colorado Springs 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 Chicago Midway Airport to Colorado Springs flights?
No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Colorado Springs.
When to book flights from Chicago Midway Airport to Colorado Springs
Cheap Chicago Midway Airport to Colorado Springs (MDW to COS) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Colorado Springs
Frequently asked questions about flying from Chicago Midway Airport to Colorado Springs
How far is Chicago Midway to Colorado Springs by plane?
Chicago Midway and Colorado Springs are 920.2 mi apart from one another. By plane, this route typically takes 2h 30m.
When did momondo last update prices for flights from Chicago Midway Airport to Colorado Springs Airport?
Prices for flights from Chicago Midway Airport to Colorado Springs Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Colorado Springs Airport?
As of October 2026, there is 1 operator available to choose from for flights from Chicago Midway Airport to Colorado Springs Airport.
How old do you have to be to fly from Chicago Midway Airport to Colorado Springs Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Colorado Springs Airport.
What documentation or ID do you need to fly to Colorado Springs Airport?
The travel and health documents you'll need for your trip to Colorado Springs Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Colorado Springs Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Colorado Springs?
Based on momondo bookings for flights between Chicago Midway Airport and Colorado Springs, the leading plane model is Embraer 175 (Enhanced Winglets), making up 20.37% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet 700 with 20.37%, Boeing 737-800 with 14.81%, and Boeing 737 MAX 8 with 12.96%.
What is the most popular airline from Chicago Midway Airport to Colorado Springs?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Colorado Springs is Southwest (100% of total bookings).
Best airlines flying from Chicago Midway Airport to Colorado Springs
Compare and see reviews for airlines that fly from Chicago Midway Airport to Colorado Springs with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $356 | Free Cancellation | Rating 7.9 4,222 reviews |
Southwest Flights From Chicago Midway Airport to Colorado Springs
Southwest flies from Chicago Midway Airport to Colorado Springs around 5 times per week, with 4,222 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Chicago Midway Airport to Colorado Springs in the last 72 hours was $356 (round-trip), much lower than the average airfare cost of $450 for Southwest flights on this route.
Traveling to a place near Colorado Springs?
Book flights to Colorado Springs if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Colorado Springs?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Colorado Springs. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Colorado Springs with flexible booking policies on momondo?
Yes. All flights to Colorado Springs from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Colorado Springs?
Once you have performed a search for Chicago to Colorado Springs flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Chicago to Colorado Springs right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Colorado Springs now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Colorado Springs and let you know when they change.