$111+ Cheap flights from Colorado Springs (COS) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Sep 17 — Sep 241
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 Wednesday
Cheap flight deals from Colorado Springs to Chicago
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Best
Last-minute
One-way
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 August 18, 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 August 18, 2026.
This United Airlines deal was found by Cheapflights users on 8/13. 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 11/712:02 pm -
Nonstop2h 51m
Tue 11/107:50 pm -
Nonstop3h 07m
Deal found 8/13![United Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 9/145:01 am -
Nonstop2h 49m
Wed 9/2310:55 am -
Nonstop2h 53m
Deal found 8/13![American Airlines logo]()
$224
This United Airlines deal was found by Cheapflights users on 8/13. 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 9/196:00 am -
1 stop4h 28m
Tue 9/228:55 am -
Nonstop2h 52m
Deal found 8/13![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 8/13. 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 11/76:00 am -
1 stop8h 17m
Tue 11/101:00 pm -
1 stop8h 27m
Deal found 8/13![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 8/13. 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 11/76:00 am -
1 stop7h 28m
Tue 11/102:44 pm -
2 stops8h 53m
Deal found 8/13![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 8/13. 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 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 11/101:20 pm -
2 stops9h 20m
Deal found 8/13![Southwest logo]()
$251
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/2912:37 pm -
Nonstop2h 53m
Wed 9/3010:55 am -
Nonstop2h 53m
Deal found 8/13![American Airlines logo]()
$258
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 9/145:01 am -
Nonstop2h 49m
Thu 9/245:00 am -
1 stop5h 22m
Deal found 8/13![American Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 8/13. 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 10/101:26 pm -
1 stop6h 26m
Sat 10/174:30 pm -
1 stop6h 52m
Deal found 8/13![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 8/13. 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 10/148:17 am -
1 stop8h 53m
Fri 10/162:03 pm -
1 stop9h 19m
Deal found 8/13![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:05 pm -
1 stop3h 55m
Mon 11/95:20 am -
1 stop6h 05m
Deal found 8/13![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:20 pm -
1 stop6h 30m
Wed 9/233:35 pm -
Nonstop2h 25m
Deal found 8/16![Southwest logo]()
$287
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 August 18, 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 August 18, 2026.
This Delta deal was found by Cheapflights users on 8/13. 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 stop6h 26m
Tue 11/101:30 pm -
1 stop7h 57m
Deal found 8/13![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Fri 10/26:03 pm -
1 stop4h 56m
Mon 10/59:03 am -
Nonstop2h 52m
Deal found 8/14![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 8/17. 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 9/236:15 am -
1 stop4h 45m
Wed 9/233:35 pm -
Nonstop2h 25m
Deal found 8/17![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 8/13. 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 11/76:00 am -
2 stops11h 00m
Tue 11/1010:22 am -
2 stops11h 05m
Deal found 8/13![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 8/16. 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.
Wed 9/91:25 pm -
1 stop6h 31m
Tue 9/158:55 am -
2 stops12h 01m
Deal found 8/16![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 8/17. 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 10/22:05 pm -
Nonstop2h 20m
Sun 10/410:00 am -
Nonstop2h 35m
Deal found 8/17![Southwest logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/17. 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 10/25:08 pm -
1 stop4h 38m
Sun 10/49:03 am -
Nonstop2h 52m
Deal found 8/17![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:40 pm -
2 stops7h 25m
Sun 11/85:20 am -
1 stop6h 05m
Deal found 8/16![Southwest logo]()
$358
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Thu 10/811:57 am -
Nonstop2h 45m
Sun 10/117:00 am -
1 stop6h 27m
Deal found 8/15![United Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 8/14. 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 10/25:00 pm -
2 stops7h 05m
Mon 10/53:45 pm -
2 stops9h 25m
Deal found 8/14![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/2311:55 am -
Nonstop2h 43m
Wed 9/238:20 pm -
1 stop4h 35m
Deal found 8/17![United Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 8/15. 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.
Thu 10/296:00 am -
2 stops11h 00m
Sun 11/16:04 am -
1 stop7h 26m
Deal found 8/15![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 8/17. 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 9/291:25 pm -
1 stop6h 31m
Tue 10/68:29 am -
2 stops12h 47m
Deal found 8/17![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 9/311:55 am -
Nonstop2h 43m
Sun 9/67:00 am -
1 stop6h 28m
Deal found 8/17![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 8/281:20 pm -
1 stop8h 16m
Wed 9/24:39 pm -
1 stop5h 59m
Deal found 8/13![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 9/28:10 am -
2 stops12h 37m
Wed 9/98:55 am -
2 stops12h 01m
Deal found 8/15![Delta logo]()
$425
Last-minute flights from Colorado Springs to ChicagoDiscover last-minute flight deals from Colorado Springs to Chicago. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Chicago. Data last updated August 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/17. 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 9/121:25 pm -
1 stop8h 19m
Tue 9/151:00 pm -
1 stop7h 56m
Deal found 8/17![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 9/145:01 am -
Nonstop2h 49m
Wed 9/2310:55 am -
Nonstop2h 53m
Deal found 8/13![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 9/145:01 am -
Nonstop2h 49m
Thu 9/245:00 am -
1 stop5h 22m
Deal found 8/13![American Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 9/1610:17 am -
1 stop8h 19m
Fri 9/186:49 pm -
Nonstop2h 51m
Deal found 8/13![American Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 9/195:01 am -
Nonstop2h 49m
Tue 9/2210:55 am -
Nonstop2h 53m
Deal found 8/13![American Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 8/13. 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 9/196:00 am -
1 stop4h 28m
Tue 9/228:55 am -
Nonstop2h 52m
Deal found 8/13![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 8/13. 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 9/1912:55 pm -
1 stop7h 01m
Tue 9/2211:17 am -
2 stops9h 39m
Deal found 8/13![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:20 pm -
1 stop6h 30m
Wed 9/233:35 pm -
Nonstop2h 25m
Deal found 8/16![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:15 pm -
Nonstop2h 15m
Tue 9/293:35 pm -
Nonstop2h 25m
Deal found 8/16![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/15. 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.
Mon 9/286:45 pm -
1 stop9h 55m
Thu 10/111:50 am -
1 stop9h 30m
Deal found 8/15![Southwest logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/2912:37 pm -
Nonstop2h 53m
Wed 9/3010:55 am -
Nonstop2h 53m
Deal found 8/13![American Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 8/17. 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 9/296:15 am -
1 stop4h 45m
Tue 10/65:45 pm -
1 stop4h 20m
Deal found 8/17![Southwest logo]()
$292
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 August 18, 2026.
Search for one-way flight options from Colorado Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 9/125:01 am -
Nonstop2h 49m
Deal found 8/13![American Airlines logo]()
$111
This Delta deal was found by Cheapflights users on 8/13. 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 9/121:25 pm -
1 stop8h 19m
Deal found 8/13![Delta logo]()
$121
This Delta deal was found by Cheapflights users on 8/13. 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 9/91:25 pm -
1 stop6h 31m
Deal found 8/13![Delta logo]()
$121
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:00 pm -
1 stop7h 25m
Deal found 8/13![Southwest logo]()
$124
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/246:03 pm -
1 stop4h 56m
Deal found 8/13![United Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 9/164:08 pm -
1 stop6h 22m
Deal found 8/13![American Airlines logo]()
$131
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 11/55:00 am -
2 stops11h 35m
Deal found 8/14![Southwest logo]()
$135
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Wed 9/1611:55 am -
Nonstop2h 43m
Deal found 8/13![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 8/14. 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.
Wed 10/1412:40 pm -
Nonstop2h 20m
Deal found 8/14![Southwest logo]()
$139
This American Airlines deal was found by Cheapflights users on 8/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:01 am -
Nonstop2h 49m
Deal found 8/16![American Airlines logo]()
$139
This Delta deal was found by Cheapflights users on 8/17. 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 9/151:25 pm -
1 stop8h 19m
Deal found 8/17![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 8/18. 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 9/158:15 am -
1 stop8h 49m
Deal found 8/18![Delta logo]()
$149
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 August 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $221 (United Airlines) |
One-way from | $111 (American Airlines) |
Popular in | July |
Cheapest in | August |
Average price | $254 |
Good round-trip deal | $344 or less |
Good one-way deal | $209 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 2,558,603 searches. Data last updated August 18, 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 - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Sat 11/7
1:26 pm-8:52 pm
1 stop6h 26m
Chicago O'Hare Intl
Tue 11/10
1:30 pm-8:27 pm
1 stop7h 57m
$241
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Sat 11/7
6:00 am-6:00 pm
2 stops11h 00m
Chicago Midway
Tue 11/10
10:22 am-8:27 pm
2 stops11h 05m
$251
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Fri 10/2
6:03 pm-11:59 pm
1 stop4h 56m
Chicago O'Hare Intl
Mon 10/5
9:03 am-10:55 am
Nonstop2h 52m
$301
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Wed 9/9
1:25 pm-8:56 pm
1 stop6h 31m
Chicago O'Hare Intl
Tue 9/15
8:55 am-7:56 pm
2 stops12h 01m
$302
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Wed 9/23
6:15 am-12:00 pm
1 stop4h 45m
Chicago Midway
Wed 9/23
3:35 pm-5:00 pm
Nonstop2h 25m
$325
Quickest round-trip
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Fri 10/2
2:05 pm-5:25 pm
Nonstop2h 20m
Chicago Midway
Sun 10/4
10:00 am-11:35 am
Nonstop2h 35m
$333
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Fri 10/2
5:08 pm-10:46 pm
1 stop4h 38m
Chicago O'Hare Intl
Sun 10/4
9:03 am-10:55 am
Nonstop2h 52m
$343
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Fri 11/6
4:40 pm-1:05 am
2 stops7h 25m
Chicago Midway
Sun 11/8
5:20 am-10:25 am
1 stop6h 05m
$358
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Fri 10/2
5:00 pm-1:05 am
2 stops7h 05m
Chicago Midway
Mon 10/5
3:45 pm-12:10 am
2 stops9h 25m
$363
Colorado SpringsChicago
COS Colorado Springs - ORD Chicago O'Hare Intl
COSORD
Colorado Springs
Thu 10/8
11:57 am-3:42 pm
Nonstop2h 45m
Chicago O'Hare Intl
Sun 10/11
7:00 am-12:27 pm
1 stop6h 27m
$365
Showing 1-10 of 35 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 August.
| 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 $286). Flying from Colorado Springs to Chicago in December is currently the most expensive (average of $453). 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 August 18, 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 August 18, 2026.
The most flights from COS to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Colorado Springs to Chicago?
Airfare is below average for this route at the moment.
Colorado Springs to Chicago flights typically cost between $243 and $317 in November.The cheapest round-trip price found within the last 5 days was $221 on United Airlines (Nov 7-Nov 10).
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 74 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 August 18, 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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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 August 18, 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 August 18, 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 2,558,603 searches. Data last updated August 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$233 | Average$381 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$234 | Average$412 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$243 | Average$373 | FlexibilityNo cancel fee | On-time71% |