$174+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Jun 18 — Jun 251
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 January or October, booked 78 days in advance, depart on a Thursday or Wednesday 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 May 19, 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 May 19, 2026.
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 8/191:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Tue 8/253:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Deal found 5/18![Southwest logo]()
$351
This American Airlines deal was found by Cheapflights users on 5/19. 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 8/2512:36 pm
COS
- ORD
Nonstop2h 54m
American Airlines
Sat 8/2910:50 am
ORD
- COS
Nonstop2h 55m
American Airlines
Deal found 5/19![American Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 5/18. 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
Wed 7/812:00 pm
MDW
- COS
1 stop8h 15m
Southwest
Deal found 5/18![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 6/2612:26 pm
COS
- ORD
Nonstop2h 49m
American Airlines
Mon 6/295:00 am
ORD
- COS
1 stop5h 53m
American Airlines
Deal found 5/19![American Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 5/15. 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 6/2612:20 pm
COS
- MDW
2 stops11h 15m
Southwest
Sat 7/44:35 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 5/18. 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.
Thu 7/231:40 pm
COS
- MDW
1 stop7h 35m
Delta
Tue 7/286:00 am
MDW
- COS
1 stop7h 32m
Delta
Deal found 5/18![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 5/18. 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.
Sat 7/256:50 am
COS
- ORD
1 stop9h 22m
Delta
Sun 7/266:35 am
ORD
- COS
1 stop6h 57m
Delta
Deal found 5/18![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 5/18. 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 6/69:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Tue 6/95:05 am
MDW
- COS
1 stop5h 50m
Southwest
Deal found 5/18![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 5/18. 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.
Fri 7/246:16 pm
COS
- MDW
2 stops13h 52m
Delta
Tue 7/286:00 am
MDW
- COS
1 stop7h 32m
Delta
Deal found 5/18![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 5/18. 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 7/218:10 am
COS
- ORD
2 stops12h 42m
Delta
Fri 7/311:44 pm
ORD
- COS
1 stop8h 23m
Delta
Deal found 5/18![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 5/17. 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 7/812:10 pm
COS
- MDW
Nonstop2h 20m
Southwest
Sun 7/128:30 am
MDW
- COS
1 stop9h 15m
Southwest
Deal found 5/17![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Tue 7/712:08 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Mon 7/139:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 5/17![United Airlines logo]()
$378
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 May 19, 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 May 19, 2026.
This United Airlines deal was found by Cheapflights users on 5/16. 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 7/812:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Mon 7/139:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 5/16![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 7/47:05 am
COS
- MDW
Nonstop2h 20m
Southwest
Mon 7/65:15 am
MDW
- COS
1 stop4h 40m
Southwest
Deal found 5/16![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 5/18. 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.
Fri 7/241:40 pm
COS
- MDW
1 stop7h 35m
Delta
Mon 7/276:00 am
MDW
- COS
1 stop7h 32m
Delta
Deal found 5/18![Delta logo]()
$371
This United Airlines deal was found by Cheapflights users on 5/16. 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.
Fri 8/1411:55 am
COS
- ORD
Nonstop2h 43m
United Airlines
Mon 8/178:46 am
ORD
- COS
Nonstop2h 47m
United Airlines
Deal found 5/16![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 5/17. 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 8/256:00 am
COS
- ORD
1 stop7h 05m
Delta
Fri 8/285:28 am
ORD
- COS
1 stop7h 47m
Delta
Deal found 5/17![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 5/16. 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 8/1411:20 am
COS
- MDW
2 stops8h 00m
Southwest
Sun 8/165:40 am
MDW
- COS
1 stop6h 55m
Southwest
Deal found 5/16![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Sat 6/1312:13 pm
COS
- ORD
Nonstop2h 46m
United Airlines
Mon 6/155:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 5/14![United Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 5/19. 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 11/148:00 am
COS
- MDW
2 stops12h 45m
Delta
Thu 11/196:00 am
MDW
- COS
1 stop7h 58m
Delta
Deal found 5/19![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/236:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Sun 6/285:00 am
MDW
- COS
1 stop6h 25m
Southwest
Deal found 5/18![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 5/15. 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.
Wed 7/16:32 pm
COS
- ORD
1 stop5h 12m
United Airlines
Wed 7/299:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 5/15![United Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 7/226:00 am
COS
- MDW
2 stops11h 18m
Delta
Wed 7/2911:05 am
MDW
- COS
2 stops12h 36m
Delta
Deal found 5/18![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/67:15 am
COS
- MDW
2 stops11h 15m
Southwest
Tue 6/95:05 am
MDW
- COS
1 stop5h 50m
Southwest
Deal found 5/17![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 5/18. 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.
Fri 7/246:00 am
COS
- ORD
2 stops12h 30m
Delta
Fri 7/317:05 am
ORD
- COS
2 stops11h 30m
Delta
Deal found 5/18![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Tue 7/75:13 pm
COS
- ORD
1 stop4h 36m
United Airlines
Mon 7/139:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 5/19![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 5/19. 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.
Wed 6/1711:20 am
COS
- MDW
2 stops8h 25m
Southwest
Wed 6/242:35 pm
MDW
- COS
2 stops8h 10m
Southwest
Deal found 5/19![Southwest logo]()
$411
This Delta deal was found by Cheapflights users on 5/15. 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 7/18:14 am
COS
- ORD
2 stops12h 11m
Delta
Wed 7/2911:30 am
ORD
- COS
2 stops12h 11m
Delta
Deal found 5/15![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 5/15. 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 6/63:42 pm
COS
- ORD
1 stop5h 12m
United Airlines
Mon 6/89:06 am
ORD
- COS
Nonstop3h 01m
United Airlines
Deal found 5/15![United Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 5/16. 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 8/257:50 am
COS
- ORD
2 stops11h 56m
Delta
Sat 8/296:51 am
ORD
- COS
2 stops11h 45m
Delta
Deal found 5/16![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 5/15. 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.
Sat 6/67:15 am
COS
- MDW
2 stops11h 15m
Southwest
Mon 6/85:20 am
MDW
- COS
1 stop6h 10m
Southwest
Deal found 5/15![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 5/15. 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.
Sat 6/279:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Sun 6/282:15 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$452
Last-minute flights from Colorado Springs to ChicagoDiscover last-minute flight deals from Colorado Springs to Chicago. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Chicago. Data last updated May 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/18. 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 6/69:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Tue 6/95:05 am
MDW
- COS
1 stop5h 50m
Southwest
Deal found 5/18![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 5/18. 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.
Thu 6/114:55 pm
COS
- MDW
2 stops7h 05m
Southwest
Thu 6/255:15 am
MDW
- COS
1 stop4h 40m
Southwest
Deal found 5/18![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 5/15. 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 6/124:55 pm
COS
- MDW
1 stop6h 15m
Southwest
Fri 6/196:40 pm
MDW
- COS
1 stop7h 40m
Southwest
Deal found 5/15![Southwest logo]()
$381
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Fri 6/123:53 pm
COS
- ORD
1 stop7h 46m
American Airlines
Tue 6/165:00 am
ORD
- COS
1 stop5h 53m
American Airlines
Deal found 5/16![American Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 5/14. 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 6/159:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Mon 6/225:00 am
ORD
- COS
1 stop4h 41m
United Airlines
Deal found 5/14![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Tue 6/169:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Tue 6/239:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Deal found 5/17![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 5/16. 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.
Fri 6/191:49 pm
COS
- ORD
1 stop5h 41m
United Airlines
Tue 6/239:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Deal found 5/16![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 5/15. 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 6/264:40 pm
COS
- MDW
1 stop7h 20m
Southwest
Sat 7/44:35 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 6/2612:26 pm
COS
- ORD
Nonstop2h 49m
American Airlines
Mon 6/295:00 am
ORD
- COS
1 stop5h 53m
American Airlines
Deal found 5/19![American Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/2612:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Sun 6/289:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 5/18![United Airlines logo]()
$378
This Southwest deal was found by Cheapflights users on 5/15. 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.
Sat 6/2712:00 pm
COS
- MDW
1 stop8h 00m
Southwest
Sun 7/55:00 am
MDW
- COS
1 stop6h 25m
Southwest
Deal found 5/15![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Tue 6/305:13 pm
COS
- ORD
1 stop4h 36m
United Airlines
Tue 7/79:03 am
ORD
- COS
Nonstop3h 03m
United Airlines
Deal found 5/17![United Airlines logo]()
$361
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 May 19, 2026.
Search for one-way flight options from Colorado Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:09 pm
COS
- ORD
2 stops11h 19m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 5/18. 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 5/18![Southwest logo]()
$176
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Sat 7/412:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Deal found 5/19![United Airlines logo]()
$176
This Southwest deal was found by Cheapflights users on 5/15. 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.
Tue 8/116:15 am
COS
- MDW
1 stop4h 45m
Southwest
Deal found 5/15![Southwest logo]()
$181
This Delta deal was found by Cheapflights users on 5/19. 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 8/141:21 pm
COS
- MDW
1 stop8h 15m
Delta
Deal found 5/19![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 5/18. 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.
Sat 8/81:21 pm
COS
- ORD
1 stop6h 25m
Delta
Deal found 5/18![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 5/18. 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.
Sat 7/46:50 am
COS
- MDW
2 stops9h 17m
Delta
Deal found 5/18![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 5/18. 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.
Thu 11/126:00 am
COS
- ORD
2 stops11h 40m
Delta
Deal found 5/18![Delta logo]()
$191
This United Airlines deal was found by Cheapflights users on 5/17. 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 5/289:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Deal found 5/17![United Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 5/15. 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.
Sat 6/131:40 pm
COS
- MDW
1 stop7h 37m
Delta
Deal found 5/15![Delta logo]()
$196
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 6/123:53 pm
COS
- ORD
1 stop6h 39m
American Airlines
Deal found 5/19![American Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 5/15. 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.
Tue 6/96:20 pm
COS
- MDW
2 stops13h 54m
Delta
Deal found 5/15![Delta logo]()
$201
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 May 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (Southwest) |
One-way from | $174 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $334 |
Good round-trip deal | $379 or less |
Good one-way deal | $216 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 May 19, 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 - ORD
COSORD
Colorado Springs
Wed 7/8
12:11 pm-3:56 pm
Nonstop2h 45m
Chicago O'Hare Intl
Mon 7/13
9:06 am-11:09 am
Nonstop3h 03m
$351
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Fri 8/14
11:55 am-3:38 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 8/17
8:46 am-10:33 am
Nonstop2h 47m
$351
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 7/4
7:05 am-10:25 am
Nonstop2h 20m
Chicago Midway
Mon 7/6
5:15 am-8:55 am
1 stop4h 40m
$361
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Sat 6/13
12:13 pm-3:59 pm
Nonstop2h 46m
Chicago O'Hare Intl
Mon 6/15
5:00 am-8:41 am
1 stop4h 41m
$361
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Wed 7/1
6:32 pm-12:44 am
1 stop5h 12m
Chicago O'Hare Intl
Wed 7/29
9:06 am-11:09 am
Nonstop3h 03m
$361
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 7/24
1:40 pm-10:15 pm
1 stop7h 35m
Chicago Midway
Mon 7/27
6:00 am-12:32 pm
1 stop7h 32m
$371
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Tue 8/25
6:00 am-2:05 pm
1 stop7h 05m
Chicago O'Hare Intl
Fri 8/28
5:28 am-12:15 pm
1 stop7h 47m
$371
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 8/14
11:20 am-8:20 pm
2 stops8h 00m
Chicago Midway
Sun 8/16
5:40 am-11:35 am
1 stop6h 55m
$376
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 11/14
8:00 am-9:45 pm
2 stops12h 45m
Chicago Midway
Thu 11/19
6:00 am-12:58 pm
1 stop7h 58m
$376
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Tue 6/23
6:10 pm-12:05 am
1 stop4h 55m
Chicago Midway
Sun 6/28
5:00 am-10:25 am
1 stop6h 25m
$381
Showing 1-10 of 41 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 May.
| 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 May 19, 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.
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 64 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 May 19, 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 19, 2026.
Other flights from Colorado Springs
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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 May 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$371 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$229 | Average$391 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$371 | FlexibilityNo cancel fee | On-time71% |