
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 |
Fly from
Fly to
Route
Depart
Return
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
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
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
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
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
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
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
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
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
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
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
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.
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.
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.
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Dominic,Mar 2026
MCO - SMF
| 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% |