Cheap flights from Colorado Springs Peterson Field to Chicago Midway

Compare Colorado Springs Peterson Field to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Colorado Springs Peterson Field to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Colorado Springs Peterson Field Airport to Chicago Midway Airport? If you want to travel next month, round-trip fares start from $386. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$256 per passenger.Departing Sat, Jun 6, returning Tue, Jun 9.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Sat, Jun 6, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Tue, Jun 9, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $256, select.

Chicago.$328 per passenger.Departing Sat, Aug 8, returning Sat, Aug 15.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Sat, Aug 8, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sat, Aug 15, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $328, select.

Chicago.$329 per passenger.Departing Thu, May 28, returning Mon, Jun 1.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Thu, May 28, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Mon, Jun 1, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $329, select.

Chicago.$368 per passenger.Departing Wed, Jul 8, returning Wed, Jul 15.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Wed, Jul 8, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Wed, Jul 15, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $368, select.

Chicago.$368 per passenger.Departing Thu, Oct 22, returning Sun, Oct 25.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Thu, Oct 22, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Oct 25, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $368, select.

Chicago.$372 per passenger.Departing Fri, Sep 11, returning Sun, Sep 13.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Fri, Sep 11, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Sep 13, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $372, select.

Chicago.$386 per passenger.Departing Fri, May 29, returning Sun, May 31.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Fri, May 29, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, May 31, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $386, select.

Chicago.$396 per passenger.Departing Fri, Jul 31, returning Sun, Aug 2.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Colorado Springs Peterson Field on Fri, Jul 31, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Aug 2, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $396, select.

Chicago.$717 per passenger.Departing Thu, Apr 30, returning Sat, May 2.Round-trip flight with Allegiant Air and Frontier Airlines.Outbound indirect flight with Allegiant Air, departing from Colorado Springs Peterson Field on Thu, Apr 30, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sat, May 2, arriving in Colorado Springs Peterson Field.Price includes taxes and charges.From $717, select.

Find the cheapest month to fly from Colorado Springs Peterson Field to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Colorado Springs Peterson Field to Chicago Midway flights are currently cheapest in June.

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Direct flights from Colorado Springs Peterson Field to Chicago Midway

Colorado Springs Peterson Field to Chicago Midway: Alternative routes

Compare routes from Colorado Springs Peterson Field to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Colorado Springs to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$256
Cheapest month to fly	June
Average flight time	2 hrs, 22 mins
Most popular airline	Southwest Airlines
Average flights per week	7

Finding cheap flights from Colorado Springs Peterson Field to Chicago Midway: Frequently asked questions

How much are round-trip flights from Colorado Springs Peterson Field to Chicago Midway?

The best price we found for a round-trip flight from Colorado Springs Peterson Field to Chicago Midway is $256. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Colorado Springs Peterson Field to Chicago Midway?

2 hours and 22 minutes is the average flight time from Colorado Springs Peterson Field to Chicago Midway.

Which airlines fly direct from Colorado Springs Peterson Field to Chicago Midway?

Southwest Airlines flies direct from Colorado Springs Peterson Field to Chicago Midway.

How many flights are there a week from Colorado Springs Peterson Field to Chicago Midway?

There are 7 flights per week flying from Colorado Springs Peterson Field to Chicago Midway, as of April 2026.

When is the cheapest time to fly from Colorado Springs Peterson Field to Chicago Midway?

The cheapest month to fly from Colorado Springs Peterson Field to Chicago Midway is usually June.

Which upcoming date is cheapest to fly from Colorado Springs Peterson Field Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Colorado Springs Peterson Field Airport to Chicago Midway Airport on Saturday, June 6, 2026.

Can I get a direct flight from Colorado Springs Peterson Field Airport to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 22 minutes.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly with from Colorado Springs Peterson Field Airport to Chicago Midway?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Colorado Springs Municipal Airport (COS) to Chicago Midway International Airport (MDW): what you need to know

Take a direct flight from Colorado Springs Municipal Airport to Chicago Midway International Airport and you'll be in the air for an average of 2 hours 20 minutes.
The timezone in Chicago is UTC-5, which is one hour ahead of Colorado Springs.
Flights from COS to MDW start at 05:00 — the earliest with Southwest Airlines. The last departure is at 16:10 with Southwest Airlines. In total, you can take your pick of six weekly Colorado Springs Municipal Airport to Chicago Midway International Airport flights.
Get to the airport on time so you don't miss your COS to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.
Flying during a peak time like July? Major public holidays and other popular periods can lead to longer lines at check-in and security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before domestic departures.
Getting to Chicago (and then discovering more of United States!) is easy with Southwest Airlines. This popular carrier offers direct flights from Colorado Springs Municipal Airport to Chicago Midway International Airport.
Most travelers choose to fly with Southwest Airlines on this route.
The most punctual carrier offering COS to MDW flights is Southwest Airlines. Its services land without delay 78.33% of the time.
We make it a cinch to book a flight with a stopover. To see your options for tickets from Colorado Springs Municipal Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight with a stop long enough to explore your chosen city. Top stopovers between COS and MDW include:
- Denver International Airport
- Dallas Love Field Airport
- Dallas/Fort Worth International Airport

How to find the cheapest flights from Colorado Springs Municipal Airport (COS) to Chicago Midway International Airport (MDW)

Currently, $127 is the lowest price we've seen for a one-way Colorado Springs Municipal Airport to Chicago Midway International Airport flight. The best price for a return ticket is $256. Keep in mind that fares could change due to availability when booking.
Get cheap tickets from COS to MDW by booking at least seven months ahead. According to our research, that's the sweet spot for picking up a bargain.
The cheapest month for flights from Colorado Springs Municipal Airport to Chicago Midway International Airport is June. Use the 'Whole month' tool to find the lowest prices if you have flexible travel dates.
Getting your hands on cheap flights from COS to MDW is a cinch with Price Alerts. All you need to do is set up one of these automatic alerts and we'll notify you as soon as a new deal comes up.
Pick your ideal arrival and departure times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to find the best deals on flights from Colorado Springs Municipal Airport to Chicago Midway International Airport.

Handy information about Colorado Springs Municipal Airport (COS)

COS is located at 7770 Milton E. Proby Parkway.
Colorado Springs Municipal Airport has an excellent on-time record, so you're less likely to experience disruptions. Departures from COS land on schedule 83.68% of the time.
To reach Colorado Springs Municipal Airport from central Colorado Springs, it'll take around 20 minutes if you're going by car. This depends on traffic though. It's approximately 16 kilometers from the airport to the city center.
Catching public transport? Expect a journey time of around 1 hour 5 minutes.
Get your travels off to a hassle-free start by staying near COS. Whether you have an early flight from Colorado Springs Municipal Airport to Chicago Midway International Airport or want to avoid feeling rushed, these stays are the answer:

Arriving at Chicago Midway International Airport (MDW)

Book a hotel near MDW if you're catching a late Colorado Springs Municipal Airport to Chicago Midway International Airport flight. Pick one of these options and avoid the hassle of a long transfer:
Get your adventure underway by picking up a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and explore beyond Chicago's main sights.
Secure the lowest price by booking your vehicle from Chicago Midway International Airport about four weeks ahead of your trip.

Getting from Chicago Midway International Airport (MDW) to central Chicago

The street address for MDW is 5700 South Cicero.
Chicago Midway International Airport is approximately 19 kilometers from the center of Chicago. The drive time takes about 20 minutes.
If you're traveling on public transport, expect a journey of around 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

July is the busiest month for flights from Colorado Springs Municipal Airport to Chicago Midway International Airport. To avoid the crowds, go to Chicago in May.
Lock in your flight from Colorado Springs Municipal Airport to Chicago Midway International Airport for July if you want to explore Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).
If you like traveling in cooler conditions, search for a cheap ticket from COS to MDW in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

You've done Chicago, now it's time to discover more of United States. Journey around 451 kilometers south-east to Columbus to check off its top sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.
Around 257 kilometers south-east of Chicago, Indianapolis is another favorite stop in United States. Get a taste of what this destination has to offer at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.