$124 Find Cheap Flights from Colorado Springs to Chicago Midway Airport - Compare and Save

Among airlines operating Colorado Springs to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Colorado Springs and Chicago Midway Airport.

Flights from Colorado Springs to Chicago Midway Airport usually depart from Colorado Springs (COS) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Colorado Springs to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $334 round-trip via Dallas Love Field (DAL), compared to $357 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Canadair (Bombardier) Regional Jet 700 family is used most often on this route, operated mainly by American Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

One-stop flights from Colorado Springs to Chicago Midway Airport most commonly connect through:

• Denver Intl (DEN) - 70% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 10% of one-stop connections
• Dallas Love Field (DAL) - 10% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 10% of one-stop connections

Denver Intl (DEN) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 52% on the Colorado Springs to Chicago Midway Airport route. Wednesday is the cheapest departure day at $311 round-trip on average, while Sunday is the most expensive at $637, a difference of $326. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Colorado Springs to Chicago Midway Airport:

• Earliest: departs at 7:55 am and lands at 10:16 am
• Latest: departs at 2:05 pm and lands at 4:26 pm.

The flight takes about 2h 21m.

A nonstop flight from Colorado Springs to Chicago Midway Airport takes 2h 21m, covering 915 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $265 to $2,120. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Colorado Springs to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $147, which is 35% below the typical average for this route.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 4h 38m, compared with 6h 12m via Dallas Love Field (DAL) and 7h 31m via Atlanta Hartsfield-Jackson (ATL).

Chicago Midway Airport is 1 hour ahead of Colorado Springs (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Colorado Springs to Chicago Midway Airport range from $298 to $474, with an average of $361 over the past 12 months. Anything below $298 counts as a good deal.