$136+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Jul 20 — Jul 271
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
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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 June 20, 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 June 20, 2026.
This Southwest deal was found by Cheapflights users on 6/19. 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 9/291:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Tue 10/63:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 6/19![Southwest logo]()
$271
This United Airlines deal was found by Cheapflights users on 6/17. 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 7/1512:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Wed 7/299:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 6/17![United Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:37 pm
COS
- ORD
Nonstop2h 53m
American Airlines
Sat 8/2910:56 am
ORD
- COS
Nonstop2h 51m
American Airlines
Deal found 6/18![American Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Wed 7/85:00 am
ORD
- COS
1 stop6h 46m
United Airlines
Deal found 6/16![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 6/19. 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 8/51:20 pm
COS
- MDW
1 stop8h 16m
Delta
Sat 8/84:39 pm
MDW
- COS
1 stop5h 59m
Delta
Deal found 6/19![Delta logo]()
$291
This American Airlines deal was found by Cheapflights users on 6/20. 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 7/155:15 pm
COS
- ORD
1 stop6h 35m
American Airlines
Wed 7/295:00 am
ORD
- COS
1 stop5h 52m
American Airlines
Deal found 6/20![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 6/17. 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.
Mon 8/106:30 am
COS
- MDW
1 stop5h 50m
Southwest
Wed 8/193:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Deal found 6/17![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:57 am
COS
- ORD
Nonstop2h 45m
United Airlines
Sat 10/109:03 am
ORD
- COS
Nonstop2h 52m
United Airlines
Deal found 6/16![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 6/19. 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 9/296:00 am
COS
- ORD
1 stop7h 32m
Delta
Tue 10/612:15 pm
ORD
- COS
2 stops10h 06m
Delta
Deal found 6/19![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 6/15. 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 7/410:23 am
COS
- ORD
1 stop5h 42m
United Airlines
Tue 7/75:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 6/15![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 6/16. 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.
Tue 8/2511:27 am
COS
- MDW
1 stop5h 34m
Delta
Sat 8/296:05 am
MDW
- COS
1 stop7h 10m
Delta
Deal found 6/16![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/17. 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.
Mon 8/104:20 pm
COS
- MDW
1 stop6h 25m
Southwest
Wed 8/123:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Deal found 6/17![Southwest logo]()
$305
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 June 20, 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 June 20, 2026.
This Delta deal was found by Cheapflights users on 6/19. 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 8/51:20 pm
COS
- MDW
1 stop8h 16m
Delta
Sat 8/84:39 pm
MDW
- COS
1 stop5h 59m
Delta
Deal found 6/19![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 6/19. 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 9/171:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Mon 9/215:40 am
MDW
- COS
1 stop6h 05m
Southwest
Deal found 6/19![Southwest logo]()
$305
This United Airlines deal was found by Cheapflights users on 6/19. 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 9/1711:55 am
COS
- ORD
Nonstop2h 43m
United Airlines
Sun 9/208:55 am
ORD
- COS
Nonstop2h 52m
United Airlines
Deal found 6/19![United Airlines logo]()
$323
This KAYAK deal was found by Cheapflights users on 6/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/133:46 pm
COS
- ORD
1 stop6h 53m
American Airlines
Thu 7/165:00 am
ORD
- COS
1 stop5h 52m
American Airlines
Deal found 6/17![American Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 6/19. 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
COS
- MDW
1 stop8h 20m
Delta
Wed 9/161:00 pm
MDW
- COS
1 stop7h 36m
Delta
Deal found 6/19![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 6/17. 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 9/45:30 am
COS
- MDW
2 stops10h 30m
Southwest
Wed 9/910:30 am
MDW
- COS
1 stop7h 05m
Southwest
Deal found 6/17![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 6/19. 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
COS
- MDW
1 stop8h 20m
Delta
Wed 9/161:00 pm
MDW
- COS
1 stop7h 36m
Delta
Deal found 6/19![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:55 am
COS
- ORD
Nonstop2h 43m
United Airlines
Sun 8/238:46 am
ORD
- COS
Nonstop2h 47m
United Airlines
Deal found 6/18![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/146:35 am
COS
- MDW
1 stop7h 05m
Southwest
Sat 7/1812:00 pm
MDW
- COS
1 stop9h 40m
Southwest
Deal found 6/16![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:07 pm
COS
- ORD
1 stop4h 42m
United Airlines
Fri 8/75:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 6/16![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 6/19. 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 7/317:55 pm
COS
- MDW
1 stop8h 30m
Southwest
Tue 8/48:20 am
MDW
- COS
1 stop5h 20m
Southwest
Deal found 6/19![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 6/19. 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 8/71:20 pm
COS
- ORD
1 stop6h 35m
Delta
Mon 8/105:30 am
ORD
- COS
1 stop7h 45m
Delta
Deal found 6/19![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/1712:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Fri 7/245:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 6/19![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 6/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:00 pm
COS
- MDW
2 stops5h 55m
Southwest
Mon 9/219:20 am
MDW
- COS
2 stops7h 20m
Southwest
Deal found 6/18![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 6/19. 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 7/221:40 pm
COS
- ORD
1 stop9h 13m
Delta
Tue 8/411:22 am
ORD
- COS
2 stops11h 16m
Delta
Deal found 6/19![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/155:35 am
COS
- MDW
2 stops7h 20m
Southwest
Wed 7/2910:15 am
MDW
- COS
2 stops10h 00m
Southwest
Deal found 6/16![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:23 am
COS
- ORD
1 stop7h 23m
United Airlines
Fri 7/34:12 pm
ORD
- COS
1 stop6h 54m
United Airlines
Deal found 6/16![United Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 6/19. 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 8/51:20 pm
COS
- ORD
1 stop6h 35m
Delta
Sat 8/811:22 am
ORD
- COS
2 stops11h 16m
Delta
Deal found 6/19![Delta logo]()
$440
This United Airlines deal was found by Cheapflights users on 6/15. 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 7/25:07 pm
COS
- ORD
1 stop6h 37m
United Airlines
Sun 7/55:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 6/15![United Airlines logo]()
$533
Last-minute flights from Colorado Springs to ChicagoDiscover last-minute flight deals from Colorado Springs to Chicago. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Chicago. Data last updated June 20, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/15. 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 7/45:44 am
COS
- ORD
Nonstop3h 01m
United Airlines
Tue 7/75:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 6/15![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:44 am
COS
- ORD
Nonstop3h 01m
United Airlines
Wed 7/89:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 6/16![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 6/15. 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.
Thu 7/92:40 pm
COS
- MDW
Nonstop2h 20m
Southwest
Tue 7/144:35 pm
MDW
- COS
1 stop6h 15m
Southwest
Deal found 6/15![Southwest logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/1412:22 pm
COS
- ORD
Nonstop2h 52m
American Airlines
Tue 7/2810:00 am
ORD
- COS
Nonstop2h 52m
American Airlines
Deal found 6/19![American Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/145:35 am
COS
- MDW
2 stops5h 50m
Southwest
Thu 7/235:15 am
MDW
- COS
1 stop4h 40m
Southwest
Deal found 6/16![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/17. 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 7/1512:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Wed 7/299:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 6/17![United Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 6/20. 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 7/155:15 pm
COS
- ORD
1 stop6h 35m
American Airlines
Wed 7/295:00 am
ORD
- COS
1 stop5h 52m
American Airlines
Deal found 6/20![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/156:10 pm
COS
- MDW
1 stop5h 00m
Southwest
Wed 7/295:35 pm
MDW
- COS
1 stop6h 25m
Southwest
Deal found 6/16![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:32 pm
COS
- ORD
1 stop5h 12m
United Airlines
Sat 7/185:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 6/18![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:15 pm
COS
- ORD
1 stop6h 35m
American Airlines
Tue 8/410:00 am
ORD
- COS
Nonstop2h 52m
American Airlines
Deal found 6/18![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:32 pm
COS
- ORD
1 stop5h 12m
United Airlines
Tue 7/289:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 6/18![United Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:22 pm
COS
- ORD
Nonstop2h 52m
American Airlines
Wed 8/510:56 am
ORD
- COS
Nonstop2h 51m
American Airlines
Deal found 6/18![American Airlines logo]()
$318
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 June 20, 2026.
Search for one-way flight options from Colorado Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Southwest deal was found by Cheapflights users on 6/15. 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.
Wed 8/121:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$136
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:22 pm
COS
- ORD
Nonstop2h 52m
American Airlines
Deal found 6/17![American Airlines logo]()
$136
This Southwest deal was found by Cheapflights users on 6/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:05 am
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/18![Southwest logo]()
$144
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/18![United Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 6/16. 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 9/161:19 pm
COS
- MDW
1 stop8h 06m
Delta
Deal found 6/16![Delta logo]()
$146
This Delta deal was found by Cheapflights users on 6/16. 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.
Tue 12/158:00 am
COS
- ORD
1 stop8h 57m
Delta
Deal found 6/16![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 6/19. 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 8/171:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/19![Southwest logo]()
$148
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:37 pm
COS
- ORD
Nonstop2h 53m
American Airlines
Deal found 6/17![American Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 6/17. 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.
Wed 8/126:00 am
COS
- MDW
2 stops11h 33m
Delta
Deal found 6/17![Delta logo]()
$151
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 6/305:13 pm
COS
- ORD
1 stop6h 31m
United Airlines
Deal found 6/15![United Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 6/19. 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 8/173:51 pm
COS
- ORD
1 stop6h 39m
American Airlines
Deal found 6/19![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 8/134:20 pm
COS
- MDW
1 stop6h 25m
Southwest
Deal found 6/16![Southwest logo]()
$158
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 June 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $271 (Southwest) |
One-way from | $136 (Southwest) |
Popular in | June |
Cheapest in | August |
Average price | $428 |
Good round-trip deal | $390 or less |
Good one-way deal | $213 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 June 20, 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 - MDW
COSMDW
Colorado Springs
Wed 8/5
1:20 pm-10:36 pm
1 stop8h 16m
Chicago Midway
Sat 8/8
4:39 pm-9:38 pm
1 stop5h 59m
$291
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 9/17
1:15 pm-4:35 pm
Nonstop2h 20m
Chicago Midway
Mon 9/21
5:40 am-10:45 am
1 stop6h 05m
$305
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Wed 9/9
1:25 pm-10:45 pm
1 stop8h 20m
Chicago Midway
Wed 9/16
1:00 pm-7:36 pm
1 stop7h 36m
$315
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 9/12
1:25 pm-10:45 pm
1 stop8h 20m
Chicago Midway
Wed 9/16
1:00 pm-7:36 pm
1 stop7h 36m
$315
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Thu 9/17
11:55 am-3:38 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 9/20
8:55 am-10:47 am
Nonstop2h 52m
$323
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 9/4
5:30 am-5:00 pm
2 stops10h 30m
Chicago Midway
Wed 9/9
10:30 am-4:35 pm
1 stop7h 05m
$336
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Tue 7/14
6:35 am-2:40 pm
1 stop7h 05m
Chicago Midway
Sat 7/18
12:00 pm-8:40 pm
1 stop9h 40m
$336
Quickest round-trip
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Fri 8/21
11:55 am-3:38 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 8/23
8:46 am-10:33 am
Nonstop2h 47m
$351
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 7/31
7:55 pm-5:25 am
1 stop8h 30m
Chicago Midway
Tue 8/4
8:20 am-12:40 pm
1 stop5h 20m
$366
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Fri 8/7
1:20 pm-8:55 pm
1 stop6h 35m
Chicago O'Hare Intl
Mon 8/10
5:30 am-12:15 pm
1 stop7h 45m
$381
Showing 1-10 of 39 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 June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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, October is the cheapest month in which you can book a flight from Colorado Springs to Chicago (average of $149). Flying from Colorado Springs to Chicago in November is currently the most expensive (average of $283). 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 June 20, 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 June 20, 2026.
The most flights from COS to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Colorado Springs to Chicago?
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 73 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 June 20, 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.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
7.9
Crew
8.6
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
Hammond
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 June 20, 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 June 20, 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 June 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$371 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$229 | Average$371 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$387 | FlexibilityNo cancel fee | On-time69% |