Cheap flights from Colorado Springs to Chicago

Flights overview

Useful information for finding cheap flights from Colorado Springs to Chicago and booking your next trip
Cheapest round-trip flights $301
United 1 stop 8 hr Sat, May 30 — Mon, Jun 1
The cheapest round-trip flight from Colorado Springs to Chicago is currently $301
Cheapest one-way flight $136
United Nonstop 4 hr Wed, Jun 3
The cheapest one-way flight from Colorado Springs to Chicago is currently $136
Cheapest nonstop flights $351
United Nonstop 4 hr Thu, Jul 9 — Sun, Jul 12
The cheapest nonstop round-trip flight from Colorado Springs to Chicago is currently $351
Last-minute weekend getaway $378
United 2 stops 14 hr Sat, May 9 — Sun, May 10
The cheapest last-minute weekend getaway from Colorado Springs to Chicago is currently $378
Cheapest business class flights $661
American Nonstop 3 hr Thu, Jul 30 — Mon, Aug 3
The cheapest business class round-trip flight from Colorado Springs to Chicago is currently $661
Fastest flight 2 hr 20 min The fastest nonstop flight from Colorado Springs to Chicago takes 2 hr 20 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Colorado Springs to Chicago is typically August. The most expensive month to fly is typically July.
August
Cheapest
Typical prices: $215–530
July
Most expensive
Typical prices: $305–570

Popular airlines from Colorado Springs to Chicago

  • Southwest
    from $322
    Typical price: $260–520
    2474 weekly connecting flights
    COS - MDW, ORD Every day
  • United
    Nonstop
    from $301
    Typical price: $250–510
    14 weekly nonstop flights
    COS - ORD Every day
    1085 weekly connecting flights
    COS - ORD Every day
  • American
    Nonstop
    from $351
    Typical price: $270–580
    8 weekly nonstop flights
    COS - ORD Every day
    304 weekly connecting flights
    COS - ORD Every day
  • Delta
    from $371
    Typical price: $315–800
    168 weekly connecting flights
    COS - MDW, ORD Every day

Popular airports near Colorado Springs

  • Colorado Springs Airport (COS)
    Colorado Springs United States 22 min 6 mi
  • Denver International Airport (DEN)
    Denver United States 1 hr 22 min 71 mi
  • Centennial Airport (APA)
    Denver United States 53 min 50 mi
  • Eagle County Regional Airport (EGE)
    Vail United States 3 hr 12 min 125 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Colorado Springs to Chicago

The cheapest flights from Colorado Springs to Chicago are usually in August. Typical ticket prices in August range from $215 to $530.
The cheapest round-trip flight from Colorado Springs to Chicago recently found on Google Flights was with United from $301. The cheapest one-way flight was with United from $136.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Colorado Springs to Chicago is $322, flying from May 30 to Jun 1.
  • The cheapest United flight from Colorado Springs to Chicago is $301, flying from May 30 to Jun 1.
  • The cheapest American flight from Colorado Springs to Chicago is $351, flying from Jul 30 to Aug 3.
  • The cheapest Delta flight from Colorado Springs to Chicago is $371, flying from Jul 23 to Jul 27.
The cheapest round-trip flight from Colorado Springs to Chicago starts at $301 from Sat, May 30 to Mon, Jun 1. The cheapest one-way flight starts at $136 and departs on Wed, Jun 3.
2 hr 20 min is the shortest flight time from Colorado Springs to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Colorado Springs to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Colorado Springs to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Colorado Springs to Chicago.

In terms of nonstop flights, United is the most popular. United offers 14 nonstop flights and 1,085 connecting flights per week. United flies from Colorado Springs Airport (COS) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 2,474 connecting flights per week. Southwest flies from Colorado Springs Airport (COS) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Colorado Springs to Chicago are:
  • American offers 8 nonstop flights and 304 connecting flights per week. American flies from Colorado Springs Airport (COS) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 168 connecting flights per week. Delta flies from Colorado Springs Airport (COS) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between Colorado Springs and Chicago.
The cheapest round-trip flight from Colorado Springs to Chicago recently found on Google Flights was with United from $301. The cheapest one-way flight was with United from $136.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Colorado Springs to Chicago is $322, flying from May 30 to Jun 1.
  • The cheapest United flight from Colorado Springs to Chicago is $301, flying from May 30 to Jun 1.
  • The cheapest American flight from Colorado Springs to Chicago is $351, flying from Jul 30 to Aug 3.
  • The cheapest Delta flight from Colorado Springs to Chicago is $371, flying from Jul 23 to Jul 27.
United and American fly direct from Colorado Springs to Chicago.
  • There are 14 United direct flights from Colorado Springs to Chicago per week. Flights are available every day.
  • There are 8 American direct flights from Colorado Springs to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Colorado Springs and Chicago at price $378 is offered by United from Sat, May 9 to Sun, May 10.
United and American fly direct from Colorado Springs to Chicago.
  • There are 14 United direct flights from Colorado Springs to Chicago per week. Flights are available every day.
  • There are 8 American direct flights from Colorado Springs to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Colorado Springs to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between Colorado Springs and Chicago start at $351 from Thu, Jul 9 to Sun, Jul 12 with United.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Colorado Springs to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Colorado Springs and Chicago start at $661 from Thu, Jul 30 to Mon, Aug 3 with American.
The cheapest economy class round-trip flights between Colorado Springs and Chicago start at $301 from Sat, May 30 to Mon, Jun 1.
To book business class trips from Colorado Springs to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Colorado Springs and Chicago starts at $378 from Sat, May 9 to Sun, May 10 with United.
The cheapest last-minute deal between Colorado Springs and Chicago at price $378 is offered by United from Sat, May 9 to Sun, May 10.
To find last-minute flight deals from Colorado Springs to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

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