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Cheap flights from Colorado Springs to Chicago from $138

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Colorado Springs to Chicago departing on 2/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Colorado Springs to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Colorado Springs to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Colorado Springs to Chicago.

Cheap last minute flights

Planning a quick getaway from Colorado Springs to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Colorado Springs to Chicago

Find recent round-trip train or bus tickets from Colorado Springs to Chicago.

All round-trip flight deals from Colorado Springs to Chicago

The cheapest plane tickets from Colorado Springs to Chicago found on KAYAK recently.
2:00 pm - 5:20 pmCOS-MDW
2h 20mnonstop
12:45 pm - 2:25 pmMDW-COS
2h 40mnonstop
$255Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
2:00 pm - 5:20 pmCOS-MDW
2h 20mnonstop
6:20 am - 11:00 amMDW-COS
5h 40m1 stop
$265Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
5:15 pm - 11:58 pmCOS-ORD
5h 43m1 stop
9:30 am - 11:37 amORD-COS
3h 07mnonstop
$265United Airlines
Find Deal
Mon, Mar 3 - Tue, Mar 4
6:00 am - 3:45 pmCOS-ORD
8h 45m1 stop
1:40 pm - 6:50 pmORD-COS
6h 10m1 stop
$275Delta
Find Deal
Thu, Feb 13 - Mon, Feb 17
2:30 pm - 10:00 pmCOS-MDW
6h 30m1 stop
12:25 pm - 8:00 pmMDW-COS
8h 35m1 stop
$275Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
8:20 am - 8:53 pmCOS-ORD
11h 33m2 stops
1:40 pm - 6:50 pmORD-COS
6h 10m1 stop
$280Delta
Find Deal
Thu, Feb 13 - Mon, Feb 17
12:13 pm - 3:57 pmCOS-ORD
2h 44mnonstop
5:00 am - 9:22 amORD-COS
5h 22m1 stop
$321American Airlines
Find Deal
Sun, Jul 20 - Wed, Aug 13
6:30 pm - 11:58 pmCOS-ORD
4h 28m1 stop
9:30 am - 11:37 amORD-COS
3h 07mnonstop
$322United Airlines
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Thu, Feb 13 - Mon, Feb 17
12:13 pm - 3:57 pmCOS-ORD
2h 44mnonstop
9:45 am - 11:30 amORD-COS
2h 45mnonstop
$342American Airlines
Find Deal
Sun, Jul 20 - Wed, Aug 13
6:24 pm - 5:46 amCOS-ORD
34h 22m3 stops
7:21 pm - 9:15 amORD-COS
14h 54m1 stop
Sun, Mar 23 - Thu, Mar 27
6:00 am - 3:45 pmCOS-ORD
8h 45m1 stop
$138Delta
Find Deal
Thu, Feb 20
6:00 am - 6:02 pmCOS-MDW
11h 02m2 stops
$143Delta
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Tue, Mar 18
8:15 am - 8:44 pmCOS-ORD
11h 29m2 stops
$143Delta
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Tue, Mar 18
10:35 am - 1:55 pmCOS-MDW
2h 20mnonstop
$148Southwest
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Sat, Feb 22
9:12 am - 12:57 pmCOS-ORD
2h 45mnonstop
$156United Airlines
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Sat, May 10
3:40 pm - 7:00 pmCOS-MDW
2h 20mnonstop
$156Southwest
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Fri, Feb 21
6:00 am - 2:53 pmCOS-MDW
7h 53m1 stop
$158Delta
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Sat, Feb 22
12:40 pm - 4:24 pmCOS-ORD
2h 44mnonstop
$163United Airlines
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Thu, Feb 20
5:03 pm - 11:59 pmCOS-ORD
5h 56m1 stop
$197American Airlines
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Mon, Feb 3
5:03 pm - 11:59 pmCOS-ORD
5h 56m1 stop
$341American Airlines
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Mon, Jan 27
12:54 pm - 4:42 pmCOS-ORD
2h 48mnonstop
9:30 am - 11:34 amORD-COS
3h 04mnonstop
$817United Airlines
Find Deal
Sat, Jan 25 - Wed, Jan 29
12:54 pm - 4:42 pmCOS-ORD
2h 48mnonstop
4:20 pm - 10:53 amORD-COS
19h 33m2 stops
$822United Airlines
Find Deal
Thu, Jan 23 - Mon, Jan 27
10:10 am - 5:05 pmCOS-ORD
5h 55m1 stop
9:30 am - 11:34 amORD-COS
3h 04mnonstop
$827United Airlines
Find Deal
Fri, Jan 24 - Thu, Jan 30
1:35 pm - 7:31 pmCOS-ORD
4h 56m1 stop
4:20 pm - 9:04 amORD-COS
17h 44m2 stops
$832United Airlines
Find Deal
Fri, Jan 24 - Thu, Jan 30
6:00 am - 1:45 pmCOS-ORD
6h 45m1 stop
1:45 pm - 7:11 pmORD-COS
6h 26m1 stop
$837Delta
Find Deal
Fri, Jan 24 - Thu, Jan 30
1:35 pm - 7:31 pmCOS-ORD
4h 56m1 stop
4:20 pm - 9:04 amORD-COS
17h 44m2 stops
$842United Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
8:20 am - 8:53 pmCOS-ORD
11h 33m2 stops
10:30 am - 9:06 pmORD-COS
11h 36m2 stops
$847Delta
Find Deal
Fri, Jan 24 - Thu, Jan 30
8:20 am - 2:25 pmCOS-MDW
5h 05m1 stop
12:45 pm - 2:25 pmMDW-COS
2h 40mnonstop
$983Southwest
Find Deal
Sat, Jan 25 - Mon, Jan 27
7:05 am - 4:10 pmCOS-MDW
8h 05m1 stop
6:20 am - 11:00 amMDW-COS
5h 40m1 stop
$993Southwest
Find Deal
Sat, Jan 25 - Mon, Jan 27
8:20 am - 6:23 pmCOS-ORD
9h 03m1 stop
2:55 pm - 9:06 pmORD-COS
7h 11m1 stop
$993Delta
Find Deal
Fri, Jan 24 - Mon, Jan 27
3:10 pm - 6:25 pmCOS-MDW
2h 15mnonstop
2:00 pm - 3:35 pmMDW-COS
2h 35mnonstop
$293Southwest
Find Deal
Mon, Mar 17 - Wed, Mar 19
12:13 pm - 3:57 pmCOS-ORD
2h 44mnonstop
9:45 am - 11:30 amORD-COS
2h 45mnonstop
$311American Airlines
Find Deal
Tue, Jul 15 - Tue, Jul 22
12:55 pm - 4:39 pmCOS-ORD
2h 44mnonstop
7:45 pm - 9:49 pmORD-COS
3h 04mnonstop
$325United Airlines
Find Deal
Wed, Mar 26 - Wed, Apr 2
1:50 pm - 5:10 pmCOS-MDW
2h 20mnonstop
12:05 pm - 1:35 pmMDW-COS
2h 30mnonstop
$331Southwest
Find Deal
Tue, Apr 22 - Fri, Apr 25
11:50 am - 3:05 pmCOS-MDW
2h 15mnonstop
8:25 am - 10:10 amMDW-COS
2h 45mnonstop
$334Southwest
Find Deal
Wed, Feb 5 - Fri, Feb 28
12:55 pm - 4:39 pmCOS-ORD
2h 44mnonstop
7:45 pm - 9:49 pmORD-COS
3h 04mnonstop
$340United Airlines
Find Deal
Thu, Mar 27 - Mon, Mar 31
12:13 pm - 3:57 pmCOS-ORD
2h 44mnonstop
9:45 am - 11:30 amORD-COS
2h 45mnonstop
$342American Airlines
Find Deal
Sun, Jul 20 - Wed, Aug 13
12:55 pm - 4:39 pmCOS-ORD
2h 44mnonstop
7:45 pm - 9:49 pmORD-COS
3h 04mnonstop
$358United Airlines
Find Deal
Thu, Mar 27 - Mon, Mar 31
2:00 pm - 5:20 pmCOS-MDW
2h 20mnonstop
12:45 pm - 2:25 pmMDW-COS
2h 40mnonstop
$373Southwest
Find Deal
Fri, Feb 7 - Sun, Feb 9
1:15 pm - 4:54 pmCOS-ORD
2h 39mnonstop
9:20 am - 11:12 amORD-COS
2h 52mnonstop
$381United Airlines
Find Deal
Mon, Jul 21 - Thu, Aug 7

United Airlines flights from Colorado Springs to Chicago

Our best United Airlines deals on Colorado Springs to Chicago flight tickets
United Airlines
Mar 3
COS5:15 pmColorado Springs
5h 43m
1 stop
ORD11:58 pmChicago O'Hare Intl
Mar 4
ORD9:30 amChicago O'Hare Intl
3h 07m
COS11:37 amColorado Springs
United Airlines
Feb 13
COS6:30 pmColorado Springs
4h 28m
1 stop
ORD11:58 pmChicago O'Hare Intl
Feb 17
ORD9:30 amChicago O'Hare Intl
3h 07m
COS11:37 amColorado Springs
United Airlines
Mar 26
COS12:55 pmColorado Springs
2h 44m
ORD4:39 pmChicago O'Hare Intl
Apr 2
ORD7:45 pmChicago O'Hare Intl
3h 04m
COS9:49 pmColorado Springs

Delta flights from Colorado Springs to Chicago

Our best Delta deals on Colorado Springs to Chicago flight tickets
Delta
Feb 13
COS6:00 amColorado Springs
8h 45m
1 stop
ORD3:45 pmChicago O'Hare Intl
Feb 17
ORD1:40 pmChicago O'Hare Intl
6h 10m
1 stop
COS6:50 pmColorado Springs
Delta
Feb 13
COS8:20 amColorado Springs
11h 33m
2 stops
ORD8:53 pmChicago O'Hare Intl
Feb 17
ORD1:40 pmChicago O'Hare Intl
6h 10m
1 stop
COS6:50 pmColorado Springs
Delta
Feb 13
COS8:20 amColorado Springs
11h 33m
2 stops
ORD8:53 pmChicago O'Hare Intl
Feb 17
ORD1:40 pmChicago O'Hare Intl
6h 10m
1 stop
COS6:50 pmColorado Springs

See travel insights to Chicago from

How to get the cheapest flight ticket from Colorado Springs to Chicago

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?

The month of February is, on average, the cheapest month to fly to Chicago from Colorado Springs, with most prices found around $312. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Colorado Springs to Chicago during January average around $316.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $496. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Colorado Springs to Chicago for around $664.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Colorado Springs to Chicago during this time can be as low as $488. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $542.

What is the cheapest Colorado Springs to Chicago flight route?

Fly from Colorado Springs to Chicago Midway for the best Colorado Springs - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Colorado Springs when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $418 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Colorado Springs for as low as $304 on momondo.

What cabin class options are available on Colorado Springs to Chicago flights?

There are 4 cabin classes available to choose from on Colorado Springs to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Colorado Springs to Chicago flight prices changed over time?

As of January 2025, prices for Colorado Springs to Chicago flights are approximately 25% more expensive when compared to flights at the same time last year.

When to book flights from Colorado Springs to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Colorado Springs to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Colorado Springs to Chicago (COS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Colorado Springs to Chicago

Best Price Found

$138

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Colorado Springs in the past 72 hours is $138. The best round-trip flight deal from Colorado Springs to Chicago found on momondo in the last 72 hours is $255.
The fastest flight from Colorado Springs to Chicago takes 2h 15m
Direct flights go from Colorado Springs to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Colorado Springs to Chicago by plane?

    Colorado Springs and Chicago are 927.0 mi apart from one another. Typically, this will take 2h 15m by plane in normal conditions.

  • When did momondo last update prices for flights from Colorado Springs Airport to Chicago?

    Prices for flights from Colorado Springs Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Colorado Springs Airport to Chicago?

  • How old do you have to be to fly from Colorado Springs Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Colorado Springs Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Colorado Springs to Chicago?

  • What is the most popular airline from Colorado Springs to Chicago?


Best airlines flying from Colorado Springs to Chicago

Compare and see reviews for airlines that fly from Colorado Springs to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $239Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $259Free CancellationRating
7.4
8,975 reviews
Search United Airlines flights
SouthwestPriceFrom $291Free CancellationRating
8.1
4,654 reviews
Search Southwest flights
  • Southwest Flights From Colorado Springs to Chicago

    Across 7 Southwest flights from Colorado Springs to Chicago this week, the average price was $384, with the best Southwest deals starting from $291 round-trip. 4,654 users have rated Southwest on momondo, with an average score of 8.1/10.

  • United Airlines Flights From Colorado Springs to Chicago

    United Airlines (7.4/10 from 8,975 reviews) operates around 7 flights from Colorado Springs to Chicago in any given week. The average United Airlines airfare for this route is around $399, with deals from around $259 rare but found on momondo. Referenced prices are for round-trip Colorado Springs to Chicago flight searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Colorado Springs to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Colorado Springs to Chicago for you.

Can I find flights from Colorado Springs to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Colorado Springs with this policy.

How can momondo help me find flights from Colorado Springs to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Colorado Springs to Chicago.

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.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago