$146+ Cheap flights from Colorado Springs (COS) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Nov 16 — Nov 231
Round-trip
1 adult, Economy
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Find cheap flights from Colorado Springs to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Colorado Springs to Chicago are usually found in August or January, booked 78 days in advance, depart on a Saturday or Thursday and return on a Monday
Cheap flight deals from Colorado Springs to Chicago
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Cheapest flights from Colorado Springs to ChicagoExplore the most affordable flight options available from Colorado Springs to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 17, 2026.
Explore the most affordable flight options available from Colorado Springs to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 17, 2026.
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:34 pm -
Nonstop2h 55m
Tue 11/1711:00 am -
Nonstop3h 04m
Deal found 10/12![American Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:09 am -
Nonstop2h 47m
Sat 11/77:50 pm -
Nonstop3h 07m
Deal found 10/13![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:31 pm -
1 stop8h 23m
Tue 11/176:00 am -
1 stop7h 26m
Deal found 10/12![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:31 pm -
1 stop6h 18m
Thu 11/125:30 am -
1 stop7h 56m
Deal found 10/13![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:26 pm -
1 stop8h 07m
Tue 11/101:05 pm -
2 stops10h 17m
Deal found 10/13![Delta logo]()
$332
This American Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:39 pm -
Nonstop2h 50m
Sun 12/1311:00 am -
Nonstop3h 09m
Deal found 10/13![American Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
2 stops9h 41m
Tue 11/1711:19 am -
2 stops10h 31m
Deal found 10/12![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:02 pm -
Nonstop2h 51m
Tue 11/107:50 pm -
Nonstop3h 07m
Deal found 10/15![United Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:09 am -
Nonstop2h 47m
Mon 11/167:50 pm -
Nonstop3h 07m
Deal found 10/12![United Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:34 pm -
Nonstop2h 55m
Sun 11/85:00 am -
1 stop8h 04m
Deal found 10/12![American Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:40 pm -
1 stop7h 30m
Sun 11/85:15 am -
1 stop7h 20m
Deal found 10/12![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:31 pm -
1 stop8h 23m
Fri 11/131:05 pm -
1 stop8h 45m
Deal found 10/16![Delta logo]()
$363
Best flights from Colorado Springs to ChicagoDiscover carefully curated flight deals from Colorado Springs to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 17, 2026.
Discover carefully curated flight deals from Colorado Springs to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 17, 2026.
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
2 stops7h 30m
Tue 11/105:50 am -
1 stop6h 25m
Deal found 10/14![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:17 am -
2 stops11h 13m
Tue 11/101:30 pm -
1 stop8h 20m
Deal found 10/12![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:02 pm -
Nonstop2h 51m
Tue 11/107:50 pm -
Nonstop3h 07m
Deal found 10/15![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:40 pm -
1 stop7h 30m
Sun 11/155:15 am -
1 stop6h 55m
Deal found 10/14![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:31 pm -
1 stop6h 18m
Sun 11/156:49 am -
1 stop6h 37m
Deal found 10/14![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:06 pm -
1 stop4h 36m
Thu 12/317:50 pm -
Nonstop3h 09m
Deal found 10/14![United Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop8h 17m
Tue 11/101:05 pm -
1 stop8h 45m
Deal found 10/16![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:30 am -
1 stop4h 49m
Wed 11/117:00 am -
1 stop4h 33m
Deal found 10/12![United Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:31 pm -
1 stop6h 18m
Wed 11/1811:19 am -
2 stops10h 31m
Deal found 10/15![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:40 pm -
2 stops7h 30m
Fri 11/205:30 pm -
1 stop5h 15m
Deal found 10/15![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:30 pm -
1 stop8h 10m
Mon 12/289:35 pm -
1 stop13h 45m
Deal found 10/12![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am -
2 stops9h 39m
Sun 11/159:30 am -
2 stops8h 58m
Deal found 10/13![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/288:05 pm -
1 stop8h 40m
Thu 12/3110:15 am -
2 stops6h 20m
Deal found 10/14![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:35 pm -
2 stops6h 40m
Sat 1/24:20 pm -
2 stops7h 20m
Deal found 10/14![Southwest logo]()
$462
Last-minute flights from Colorado Springs to ChicagoDiscover last-minute flight deals from Colorado Springs to Chicago. Data last updated October 17, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Chicago. Data last updated October 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:34 pm -
Nonstop2h 55m
Sun 11/85:00 am -
1 stop8h 04m
Deal found 10/12![American Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:40 pm -
1 stop7h 30m
Sun 11/85:15 am -
1 stop7h 20m
Deal found 10/12![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:09 am -
Nonstop2h 47m
Sat 11/77:50 pm -
Nonstop3h 07m
Deal found 10/13![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:26 pm -
1 stop8h 07m
Tue 11/101:05 pm -
2 stops10h 17m
Deal found 10/13![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:02 pm -
Nonstop2h 51m
Tue 11/107:50 pm -
Nonstop3h 07m
Deal found 10/15![United Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:09 am -
Nonstop2h 47m
Tue 11/107:50 pm -
Nonstop3h 07m
Deal found 10/14![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:31 pm -
1 stop6h 18m
Thu 11/125:30 am -
1 stop7h 56m
Deal found 10/13![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:09 am -
Nonstop2h 47m
Mon 11/167:50 pm -
Nonstop3h 07m
Deal found 10/12![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:31 pm -
1 stop8h 23m
Thu 11/126:00 am -
1 stop7h 26m
Deal found 10/16![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:34 pm -
Nonstop2h 55m
Tue 11/1711:00 am -
Nonstop3h 04m
Deal found 10/12![American Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:31 pm -
1 stop8h 23m
Tue 11/176:00 am -
1 stop7h 26m
Deal found 10/12![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
2 stops9h 41m
Tue 11/1711:19 am -
2 stops10h 31m
Deal found 10/12![Delta logo]()
$337
One-way flights from Colorado Springs to ChicagoSearch for one-way flight options from Colorado Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
Search for one-way flight options from Colorado Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:10 pm -
2 stops23h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:34 am -
1 stop21h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:10 pm -
2 stops23h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:34 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![American Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:10 pm -
2 stops23h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:39 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:38 pm -
1 stop21h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:10 pm -
2 stops28h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$159
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:31 pm -
1 stop8h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$164
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:20 pm -
1 stop4h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![United Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:10 pm -
2 stops40h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/103:01 pm -
1 stop27h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$165
Find flight deals from Colorado Springs to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Colorado Springs (COS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (American Airlines) |
One-way from | $146 (Kiwi.com) |
Popular in | July |
Cheapest in | August |
Average price | $382 |
Good round-trip deal | $382 or less |
Good one-way deal | $275 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Colorado Springs to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 17, 2026.
Use the filters below to find and compare flights from Colorado Springs to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Wed 11/11
1:31 pm-10:54 pm
1 stop8h 23m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Fri 11/13
1:20 pm-6:38 pm
1 stop4h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 12/8
1:40 pm-10:54 pm
1 stop8h 14m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Tue 1/12
7:05 am-1:11 pm
1 stop5h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Sat 12/12
1:40 pm-8:53 pm
1 stop6h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Thu 1/14
8:00 am-3:27 pm
1 stop6h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Tue 1/12
8:00 am-3:27 pm
1 stop6h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Mon 1/11
5:55 pm-8:34 am
2 stops13h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Tue 12/8
12:59 pm-10:15 pm
1 stop8h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Wed 11/11
8:00 am-4:00 pm
1 stop7h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
Showing 1-10 of 29 resultsSorted by cheapest first
Compare providers for flights from Colorado Springs to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Colorado Springs to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Colorado Springs-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Colorado Springs-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Colorado Springs-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Colorado Springs-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Colorado Springs-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Colorado Springs to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Colorado Springs with our price prediction graph.
COS-CHI
COS-ORD
COS-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Colorado Springs to Chicago
COS-CHI
COS-ORD
COS-MDW
What is the cheapest month to book a flight from Colorado Springs to Chicago?
Currently, January is the cheapest month in which you can book a flight from Colorado Springs to Chicago (average of $279). Flying from Colorado Springs to Chicago in June is currently the most expensive (average of $451). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from COS to CHI?
Find hourly flight availability from Colorado Springs to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 17, 2026.
When flying from Colorado Springs to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Colorado Springs to Chicago
Explore weekly flight availability from Colorado Springs to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 17, 2026.
The most flights from COS to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Colorado Springs to Chicago?
Airfare is typical for this route at the moment.
Colorado Springs to Chicago flights typically cost between $299 and $483 in November.The cheapest round-trip price found within the last 5 days was $304 on American Airlines (Nov 10-Nov 17).
How far ahead should I book a flight from Colorado Springs to Chicago?
The price you pay for your flight from Colorado Springs to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 76 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated October 17, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Colorado Springs to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Colorado Springs to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Colorado Springs and Chicago flights
Browse other Colorado Springs and Chicago flight options. Last updated on October 17, 2026.
Other flights from Colorado Springs
Browse through other flights departing from Colorado Springs. Flights are based on user searches made on Cheapflights and were last updated on October 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Colorado Springs to Chicago
Discover the top 3 airlines that operate flights from Colorado Springs to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$353 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$243 | Average$429 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$243 | Average$385 | FlexibilityNo cancel fee | On-time63% |