$136+ Cheap flights from Chicago (CHI) to Colorado Springs (COS)
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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Jun 5 — Jun 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Colorado Springs 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 Chicago to Colorado Springs are usually found in November or January, booked 28 days in advance, depart on a Saturday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Colorado Springs
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Colorado SpringsExplore the most affordable flight options available from Chicago to Colorado Springs. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
Explore the most affordable flight options available from Chicago to Colorado Springs. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
This United Airlines deal was found by Cheapflights users on 5/1. 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 6/29:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Tue 6/99:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Deal found 5/1![United Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 5/2. 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 6/19:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Tue 6/99:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Deal found 5/2![United Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 5/5. 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 8/129:06 am
ORD
- COS
Nonstop2h 53m
United Airlines
Tue 8/1812:45 pm
COS
- ORD
Nonstop2h 44m
United Airlines
Deal found 5/5![United Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 5/5. 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 9/99:06 am
ORD
- COS
Nonstop2h 53m
United Airlines
Sat 9/1212:45 pm
COS
- ORD
Nonstop2h 44m
United Airlines
Deal found 5/5![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 5/5. 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 10/213:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Mon 10/262:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 5/5![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 5/4. 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 6/19:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Thu 6/412:13 pm
COS
- ORD
Nonstop2h 46m
United Airlines
Deal found 5/4![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 5/3. 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 6/22:15 pm
MDW
- COS
1 stop9h 05m
Southwest
Tue 6/96:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Deal found 5/3![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 5/1. 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 6/22:00 pm
ORD
- COS
2 stops9h 22m
Delta
Tue 6/96:00 am
COS
- ORD
1 stop7h 16m
Delta
Deal found 5/1![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 5/5. 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 10/219:20 am
ORD
- COS
Nonstop2h 58m
United Airlines
Mon 10/265:13 pm
COS
- ORD
1 stop5h 44m
United Airlines
Deal found 5/5![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 5/5. 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 10/213:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Wed 10/216:55 pm
COS
- MDW
1 stop9h 50m
Southwest
Deal found 5/5![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 5/1. 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 5/231:44 pm
ORD
- COS
2 stops9h 38m
Delta
Wed 5/2711:55 am
COS
- ORD
1 stop5h 55m
Delta
Deal found 5/1![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 5/2. 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 6/31:22 pm
MDW
- COS
2 stops9h 05m
Delta
Mon 6/81:40 pm
COS
- MDW
1 stop7h 37m
Delta
Deal found 5/2![Delta logo]()
$306
Best flights from Chicago to Colorado SpringsDiscover carefully curated flight deals from Chicago to Colorado Springs that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
Discover carefully curated flight deals from Chicago to Colorado Springs that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
This Delta deal was found by Cheapflights users on 5/3. 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 6/22:00 pm
ORD
- COS
2 stops9h 22m
Delta
Tue 6/96:00 am
COS
- ORD
1 stop7h 16m
Delta
Deal found 5/3![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 5/3. 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
MDW
- COS
1 stop9h 20m
Southwest
Tue 6/166:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Deal found 5/3![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 5/1. 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 6/49:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Sun 6/712:13 pm
COS
- ORD
Nonstop2h 46m
United Airlines
Deal found 5/1![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 5/2. 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 6/1012:00 pm
MDW
- COS
1 stop8h 15m
Southwest
Fri 6/2612:20 pm
COS
- MDW
1 stop10h 05m
Southwest
Deal found 5/2![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 5/4. 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 6/196:40 pm
MDW
- COS
1 stop7h 40m
Southwest
Wed 6/246:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Deal found 5/4![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 5/1. 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 6/193:22 pm
ORD
- COS
1 stop6h 45m
Delta
Mon 6/226:20 pm
COS
- ORD
2 stops12h 45m
Delta
Deal found 5/1![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 5/5. 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 7/46:15 am
MDW
- COS
1 stop9h 10m
Southwest
Tue 7/77:05 pm
COS
- MDW
1 stop9h 20m
Southwest
Deal found 5/5![Southwest logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Thu 6/2512:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Deal found 5/5![United Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/198:46 am
ORD
- COS
Nonstop3h 01m
United Airlines
Sat 5/2312:16 pm
COS
- ORD
Nonstop2h 46m
United Airlines
Deal found 5/1![United Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 5/5. 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 7/168:27 am
ORD
- COS
2 stops10h 08m
Delta
Mon 7/206:16 pm
COS
- ORD
2 stops12h 43m
Delta
Deal found 5/5![Delta logo]()
$431
This Southwest deal was found by Cheapflights users on 5/4. 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 6/185:20 am
MDW
- COS
1 stop6h 10m
Southwest
Thu 6/254:55 pm
COS
- MDW
1 stop6h 15m
Southwest
Deal found 5/4![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 5/3. 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 7/229:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Sat 7/2512:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Deal found 5/3![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:30 am
ORD
- COS
1 stop8h 05m
Delta
Sat 6/206:50 am
COS
- ORD
1 stop9h 06m
Delta
Deal found 5/2![Delta logo]()
$445
This Southwest deal was found by Cheapflights users on 5/5. 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 6/2612:30 pm
MDW
- COS
Nonstop2h 30m
Southwest
Thu 7/22:40 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 5/5![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 5/5. 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 7/239:06 am
ORD
- COS
Nonstop3h 03m
United Airlines
Mon 7/2712:11 pm
COS
- ORD
Nonstop2h 45m
United Airlines
Deal found 5/5![United Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 5/1. 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 6/15:30 am
MDW
- COS
1 stop5h 30m
Southwest
Thu 6/44:55 pm
COS
- MDW
1 stop6h 15m
Southwest
Deal found 5/1![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/168:40 am
ORD
- COS
1 stop4h 46m
United Airlines
Wed 5/2011:43 am
COS
- ORD
Nonstop2h 44m
United Airlines
Deal found 5/1![United Airlines logo]()
$443
This Southwest deal was found by Cheapflights users on 5/5. 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.
Sun 6/215:00 am
MDW
- COS
1 stop6h 25m
Southwest
Thu 6/254:40 pm
COS
- MDW
1 stop7h 20m
Southwest
Deal found 5/5![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 5/5. 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 5/292:40 pm
ORD
- COS
2 stops8h 35m
Southwest
Tue 6/27:05 am
COS
- ORD
2 stops10h 45m
Southwest
Deal found 5/5![Southwest logo]()
$424
Last-minute flights from Chicago to Colorado SpringsDiscover last-minute flight deals from Chicago to Colorado Springs. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Colorado Springs. Data last updated May 6, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/1. 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 5/231:44 pm
ORD
- COS
2 stops9h 38m
Delta
Wed 5/2711:55 am
COS
- ORD
1 stop5h 55m
Delta
Deal found 5/1![Delta logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/6. 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 5/285:00 am
ORD
- COS
1 stop5h 54m
American Airlines
Sat 5/303:45 pm
COS
- ORD
1 stop6h 52m
American Airlines
Deal found 5/6![American Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 5/2. 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 6/19:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Tue 6/99:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Deal found 5/2![United Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 5/4. 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 6/19:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Thu 6/412:13 pm
COS
- ORD
Nonstop2h 46m
United Airlines
Deal found 5/4![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 5/3. 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 6/16:25 pm
MDW
- COS
1 stop6h 25m
Southwest
Thu 6/44:40 pm
COS
- MDW
1 stop7h 20m
Southwest
Deal found 5/3![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:59 pm
ORD
- COS
1 stop7h 28m
Delta
Mon 6/86:00 am
COS
- ORD
2 stops12h 31m
Delta
Deal found 5/4![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 5/1. 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 6/29:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Tue 6/99:00 am
COS
- ORD
Nonstop3h 03m
United Airlines
Deal found 5/1![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 5/3. 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 6/22:15 pm
MDW
- COS
1 stop9h 05m
Southwest
Tue 6/96:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Deal found 5/3![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 5/1. 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 6/22:00 pm
ORD
- COS
2 stops9h 22m
Delta
Tue 6/96:00 am
COS
- ORD
1 stop7h 16m
Delta
Deal found 5/1![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 5/2. 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 6/31:22 pm
MDW
- COS
2 stops9h 05m
Delta
Mon 6/81:40 pm
COS
- MDW
1 stop7h 37m
Delta
Deal found 5/2![Delta logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/64:45 pm
ORD
- COS
1 stop6h 39m
American Airlines
Mon 6/85:15 pm
COS
- ORD
1 stop6h 24m
American Airlines
Deal found 5/3![American Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 5/4. 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 6/196:40 pm
MDW
- COS
1 stop7h 40m
Southwest
Wed 6/246:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Deal found 5/4![Southwest logo]()
$331
One-way flights from Chicago to Colorado SpringsSearch for one-way flight options from Chicago to Colorado Springs. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
Search for one-way flight options from Chicago to Colorado Springs. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This American Airlines deal was found by Cheapflights users on 5/4. 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 7/110:00 am
ORD
- COS
Nonstop2h 56m
American Airlines
Deal found 5/4![American Airlines logo]()
$136
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/29:06 am
ORD
- COS
Nonstop3h 04m
United Airlines
Deal found 5/5![United Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 5/4. 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 7/11:46 pm
ORD
- COS
1 stop8h 21m
Delta
Deal found 5/4![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 5/4. 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 7/112:00 pm
MDW
- COS
1 stop8h 15m
Southwest
Deal found 5/4![Southwest logo]()
$146
This Delta deal was found by Cheapflights users on 5/4. 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 5/272:00 pm
ORD
- COS
2 stops9h 22m
Delta
Deal found 5/4![Delta logo]()
$151
This Delta deal was found by Cheapflights users on 5/4. 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 5/271:22 pm
MDW
- COS
2 stops10h 00m
Delta
Deal found 5/4![Delta logo]()
$151
This Southwest deal was found by Cheapflights users on 5/5. 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 6/26:10 am
MDW
- COS
1 stop7h 25m
Southwest
Deal found 5/5![Southwest logo]()
$154
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/69:40 am
ORD
- COS
1 stop6h 21m
American Airlines
Deal found 5/5![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 5/6. 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 5/286:25 pm
MDW
- COS
1 stop6h 25m
Southwest
Deal found 5/6![Southwest logo]()
$156
This Delta deal was found by Cheapflights users on 5/5. 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 6/39:49 am
ORD
- COS
2 stops13h 33m
Delta
Deal found 5/5![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 5/6. 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 5/282:00 pm
ORD
- COS
2 stops9h 22m
Delta
Deal found 5/6![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 5/6. 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 5/281:59 pm
MDW
- COS
2 stops9h 23m
Delta
Deal found 5/6![Delta logo]()
$161
Find flight deals from Chicago to Colorado Springs
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Colorado Springs (COS). 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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $271 (United Airlines) |
One-way from | $136 (American Airlines) |
Popular in | February |
Cheapest in | November |
Average price | $377 |
Good round-trip deal | $371 or less |
Good one-way deal | $188 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Colorado Springs 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 6, 2026.
Use the filters below to find and compare flights from Chicago to Colorado Springs that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoColorado Springs
ORD - COS
ORDCOS
Chicago O'Hare Intl
Tue 6/2
2:00 pm-10:22 pm
2 stops9h 22m
Colorado Springs
Tue 6/9
6:00 am-2:16 pm
1 stop7h 16m
$330
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Fri 6/12
4:55 pm-1:15 am
1 stop9h 20m
Colorado Springs
Tue 6/16
6:10 pm-12:05 am
1 stop4h 55m
$331
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Wed 6/10
12:00 pm-7:15 pm
1 stop8h 15m
Colorado Springs
Fri 6/26
12:20 pm-11:25 pm
1 stop10h 05m
$331
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Fri 6/19
6:40 pm-1:20 am
1 stop7h 40m
Colorado Springs
Wed 6/24
6:10 pm-12:05 am
1 stop4h 55m
$331
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Sat 7/4
6:15 am-2:25 pm
1 stop9h 10m
Colorado Springs
Tue 7/7
7:05 pm-5:25 am
1 stop9h 20m
$339
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Thu 6/18
5:20 am-10:30 am
1 stop6h 10m
Colorado Springs
Thu 6/25
4:55 pm-12:10 am
1 stop6h 15m
$371
Quickest round-trip
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Fri 6/26
12:30 pm-2:00 pm
Nonstop2h 30m
Colorado Springs
Thu 7/2
2:40 pm-6:00 pm
Nonstop2h 20m
$371
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Mon 6/1
5:30 am-10:00 am
1 stop5h 30m
Colorado Springs
Thu 6/4
4:55 pm-12:10 am
1 stop6h 15m
$371
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Sun 6/21
5:00 am-10:25 am
1 stop6h 25m
Colorado Springs
Thu 6/25
4:40 pm-1:00 am
1 stop7h 20m
$371
ChicagoColorado Springs
ORD - COS
ORDCOS
Chicago O'Hare Intl
Fri 6/19
3:22 pm-9:07 pm
1 stop6h 45m
Colorado Springs
Mon 6/22
6:20 pm-8:05 am
2 stops12h 45m
$386
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Chicago to Colorado Springs
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 Chicago to Colorado Springs 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 Chicago-Colorado Springs flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Colorado Springs flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Colorado Springs flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Colorado Springs 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 Chicago-Colorado Springs 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 Chicago to Colorado Springs
Have a flexible travel schedule? Discover the best time to fly to Colorado Springs from Chicago with our price prediction graph.
CHI-COS
ORD-COS
MDW-COS
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 Chicago to Colorado Springs
CHI-COS
ORD-COS
MDW-COS
How far ahead should I book a flight from Chicago to Colorado Springs?
The best time to book flights from Chicago to Colorado Springs is 75 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Colorado Springs?
Currently, December is the cheapest month in which you can book a flight from Chicago to Colorado Springs (average of $105). Flying from Chicago to Colorado Springs in July is currently the most expensive (average of $239). 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 CHI to COS?
Find hourly flight availability from Chicago to Colorado Springs. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.
It’s optimal to fly from Chicago to Colorado Springs in the afternoon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the evening.
Weekly flight availability from Chicago to Colorado Springs
Explore weekly flight availability from Chicago to Colorado Springs. 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 May 6, 2026.
The most flights from CHI to COS are scheduled on a Tuesday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago to Colorado Springs?
Reviews of airlines servicing Colorado Springs
Get insights into the airlines that provide service to Colorado Springs. 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 Colorado Springs. Reviews last updated May 6, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Colorado Springs by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Colorado Springs. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Colorado Springs flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Colorado Springs
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Colorado Springs
Explore flights to Colorado Springs departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Complete your trip
Complete your trip to Colorado Springs by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Colorado Springs by cabin class
Find flights from Chicago to Colorado Springs, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Colorado Springs flights
Browse other Chicago and Colorado Springs flight options. Last updated on May 6, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Colorado Springs
Discover the top 3 airlines that operate flights from Chicago to Colorado Springs. 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$193 | Average$323 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$246 | Average$383 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$274 | Average$398 | FlexibilityNo cancel fee | On-time63% |