Cheap Flights from Colorado Springs, CO to Chicago, IL from $244

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On Cheapflightsplus.com you will find 3 direct and 109 connecting flights from Colorado Springs to Chicago. You can compare airfare deals from 1 airlines and multiple travel sites from $244, book and save on cheap plane tickets and last minute offers. Also check out COS-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Colorado Springs to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $244 (one-way), $418 (round-trip).

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Best Flights from Colorado Springs to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Colorado Springs to Chicago with the lowest price of $244. The fastest direct flight takes 2h 44m and the fastest connecting – 4h 18m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $244 Find flight	09:00 Colorado Springs Colorado Springs	12:54 Chicago O'Hare International	2h 54m	United Airlines	UA4647
from $245 Find flight	12:40 Colorado Springs Colorado Springs	16:24 Chicago O'Hare International	2h 44m	United Airlines	UA5529
from $281 Find flight	09:00 Colorado Springs Colorado Springs	12:54 Chicago O'Hare International	2h 54m	United Airlines	UA4628
from $249 Find flight	10:00 Colorado Springs Colorado Springs	22:51 Chicago O'Hare International	11h 51m layover 8h 19m - Denver	United Airlines	UA5548 UA2258
from $249 Find flight	18:32 Colorado Springs Colorado Springs	09:31+1 день Chicago O'Hare International	13h 59m layover 10h 22m - Denver	United Airlines	UA4774 UA532
from $249 Find flight	07:15 Colorado Springs Colorado Springs	22:51 Chicago O'Hare International	14h 36m layover 11h 4m - Denver	United Airlines	UA523 UA2258
from $249 Find flight	17:17 Colorado Springs Colorado Springs	09:31+1 день Chicago O'Hare International	15h 14m layover 11h 36m - Denver	United Airlines	UA5235 UA532
from $249 Find flight	07:15 Colorado Springs Colorado Springs	00:22+1 день Chicago O'Hare International	16h 7m layover 12h 34m - Denver	United Airlines	UA523 UA377
from $256 Find flight	17:17 Colorado Springs Colorado Springs	22:51 Chicago O'Hare International	4h 34m layover 0h 56m - Denver	United Airlines	UA5235 UA2258
from $256 Find flight	13:22 Colorado Springs Colorado Springs	19:24 Chicago O'Hare International	5h 2m layover 1h 37m - Denver	United Airlines	UA251 UA234
from $256 Find flight	17:17 Colorado Springs Colorado Springs	00:22+1 день Chicago O'Hare International	6h 5m layover 2h 26m - Denver	United Airlines	UA5235 UA377
from $256 Find flight	11:35 Colorado Springs Colorado Springs	19:24 Chicago O'Hare International	6h 49m layover 3h 17m - Denver	United Airlines	UA5902 UA234
from $258 Find flight	09:20 Colorado Springs Colorado Springs	14:50 Chicago O'Hare International	4h 30m layover 0h 43m - Denver	United Airlines	UA4693 UA2312
from $258 Find flight	07:30 Colorado Springs Colorado Springs	13:18 Chicago O'Hare International	4h 48m layover 1h 10m - Denver	United Airlines	UA523 UA2329
from $290 Find flight	10:45 Colorado Springs Colorado Springs	19:24 Chicago O'Hare International	7h 39m layover 4h 7m - Denver	United Airlines	UA4673 UA234
from $335 Find flight	08:30 Colorado Springs Colorado Springs	14:46 Chicago O'Hare International	5h 16m layover 1h 38m - Denver	United Airlines	UA4711 UA2312

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 09, 2025

Flight Schedule Colorado Springs (Colorado) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Colorado Springs to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
09:00 — 12:54	09:00 — 12:54 UA4647 United Airlines Colorado Springs — Chicago	2h 54m	Find flight from$244
09:00 — 12:54	09:00 — 12:54 UA4628 United Airlines Colorado Springs — Chicago	2h 54m	Find flight from$281
12:40 — 16:24	12:40 — 16:24 UA5529 United Airlines Colorado Springs — Chicago	2h 44m	Find flight from$245
05:30 — 11:20	05:30 — 06:37 UA4696 United Airlines Colorado Springs — Denver 1h 12m stop 07:49 — 11:20 UA288 United Airlines Denver — Chicago	4h 50m including layover	Find flight from$293
06:00 — 11:20	06:00 — 07:05 UA5291 United Airlines Colorado Springs — Denver 40m stop 07:50 — 11:29 UA1811 United Airlines Denver — Chicago	4h 20m including layover	Find flight from$271
06:00 — 22:51	06:00 — 07:05 UA5291 United Airlines Colorado Springs — Denver 12h 15m stop 19:20 — 22:51 UA2258 United Airlines Denver — Chicago	15h 51m including layover	Find flight from$281
07:15 — 22:51	07:15 — 08:16 UA523 United Airlines Colorado Springs — Denver 11h 4m stop 19:20 — 22:51 UA2258 United Airlines Denver — Chicago	14h 36m including layover	Find flight from$249
07:15 — 00:22 +1 day	07:15 — 08:16 UA523 United Airlines Colorado Springs — Denver 12h 34m stop 20:50 — 00:22 UA377 United Airlines Denver — Chicago	16h 7m including layover	Find flight from$249
08:30 — 22:51	08:30 — 09:37 UA4711 United Airlines Colorado Springs — Denver 9h 43m stop 19:20 — 22:51 UA2258 United Airlines Denver — Chicago	13h 21m including layover	Find flight from$249
08:30 — 00:22 +1 day	08:30 — 09:37 UA4711 United Airlines Colorado Springs — Denver 11h 13m stop 20:50 — 00:22 UA377 United Airlines Denver — Chicago	14h 52m including layover	Find flight from$249
09:20 — 14:50	09:20 — 10:32 UA4693 United Airlines Colorado Springs — Denver 43m stop 11:20 — 14:55 UA2312 United Airlines Denver — Chicago	4h 30m including layover	Find flight from$258
10:00 — 22:51	10:00 — 11:01 UA5548 United Airlines Colorado Springs — Denver 8h 19m stop 19:20 — 22:51 UA2258 United Airlines Denver — Chicago	11h 51m including layover	Find flight from$249
10:00 — 00:22 +1 day	10:00 — 11:01 UA5548 United Airlines Colorado Springs — Denver 9h 49m stop 20:50 — 00:22 UA377 United Airlines Denver — Chicago	13h 22m including layover	Find flight from$249
11:35 — 19:24	11:35 — 12:36 UA5902 United Airlines Colorado Springs — Denver 3h 17m stop 15:53 — 19:24 UA234 United Airlines Denver — Chicago	6h 49m including layover	Find flight from$256
11:40 — 16:58	10:45 — 11:46 UA4673 United Airlines Colorado Springs — Denver 40m stop 13:30 — 17:01 UA617 United Airlines Denver — Chicago	4h 18m including layover	Find flight from$256
13:22 — 19:24	13:22 — 14:16 UA251 United Airlines Colorado Springs — Denver 1h 37m stop 15:53 — 19:24 UA234 United Airlines Denver — Chicago	5h 2m including layover	Find flight from$256
13:35 — 19:31	13:35 — 14:33 UA2294 United Airlines Colorado Springs — Denver 1h 22m stop 15:55 — 19:31 UA1495 United Airlines Denver — Chicago	4h 56m including layover	Find flight from$258
15:30 — 21:25	15:30 — 16:31 UA5450 United Airlines Colorado Springs — Denver 1h 24m stop 17:55 — 21:25 UA1898 United Airlines Denver — Chicago	4h 55m including layover	Find flight from$258
15:30 — 21:25	15:30 — 16:28 UA596 United Airlines Colorado Springs — Denver 1h 27m stop 17:55 — 21:25 UA1898 United Airlines Denver — Chicago	4h 55m including layover	Find flight from$258
17:17 — 09:31 +1 day	17:17 — 18:24 UA5235 United Airlines Colorado Springs — Denver 11h 36m stop 06:00 — 09:31 UA532 United Airlines Denver — Chicago	15h 14m including layover	Find flight from$249
17:17 — 22:51	17:17 — 18:24 UA5235 United Airlines Colorado Springs — Denver 56m stop 19:20 — 22:51 UA2258 United Airlines Denver — Chicago	4h 34m including layover	Find flight from$256
18:32 — 09:31 +1 day	18:32 — 19:38 UA4774 United Airlines Colorado Springs — Denver 10h 22m stop 06:00 — 09:31 UA532 United Airlines Denver — Chicago	13h 59m including layover	Find flight from$249
18:34 — 23:57	18:34 — 19:40 UA4774 United Airlines Colorado Springs — Denver 45m stop 20:25 — 23:57 UA377 United Airlines Denver — Chicago	4h 23m including layover	Find flight from$293

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on May 9, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Colorado Springs to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Colorado Springs and Chicago is 1484 miles. Time difference between the cities is 1h. Airplanes depart 05:30 to 18:34 from 3 Colorado Springs airports and arrive 05:30 to 18:34 to 7 Chicago airports. Average flight time is 2h 54m.

The fastest flight 2h 44m
Average flight time 2h 54m
The earliest flight 05:30
The latest flight 18:34
Distance 923 ml

The cheapest months to travel to Chicago are december (from 244 $), january (from 258 $), february (from 258 $).

The most expensive months are november (from 281 $), february (from 258 $), january (from 258 $).

What is the lowest airfare Colorado Springs to Chicago?

The cheapest plane ticket found by our users is $244. This airfare is for economy class on one-way UA4647 flight by United Airlines for December 12, 2024 which leaves Colorado Springs in Colorado Springs at 09:00 am and arrives at Chicago O'Hare International at 12:54.

Economy class

$244

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Business class

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First class

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Popular Airlines on the Route

The flight Colorado Springs — Chicago is served by 1 regular airline . Most of the flights on this route are operated by United Airlines - 112 departures per week at the price of from $ 244 . And the most expensive tickets are offered by United Airlines airline - from $ 873.

Direct flights

There are 3 nonstop flights on the route. The fastest direct flight is UA5529 by United Airlines takes 2h 44m and the cheapest is UA4647 by United Airlines for $244.

UA - United Airlines

from $244

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Connecting Flights

There are 109 flights with layovers on the route. The fastest connecting flight is UA4673 by United Airlines takes 4h 18m and the cheapest is UA4647 by United Airlines for $249.

UA - United Airlines

from $249

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Airports

You can fly from Colorado Springs to Chicago from 3 airports (USAF Academy Airstrip, Colorado Springs, Butts AAF).

Colorado Springs airports

USAF Academy Airstrip-AFF

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Colorado Springs-COS

from $244
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Butts AAF-FCS

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Colorado Springs by 1 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Colorado Springs

You may also consider searching for discounted plane tickets to some other popular places from Colorado Springs within United States.

Colorado Springs — Las Vegas

from $69

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Colorado Springs — Phoenix

from $54

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Colorado Springs — Dallas

from $79

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Colorado Springs — Houston

from $59

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Colorado Springs — San Antonio

from $67

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Colorado Springs — Chicago

from $73

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Colorado Springs — Orlando

from $60

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Colorado Springs — Seattle

from $68

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Colorado Springs — San Diego

from $58

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Colorado Springs — Denver

from $67

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Top International Destinations from Colorado Springs

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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