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Find Cheap Flights from Colorado Springs to Chicago (COS - CHI)

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Colorado Springs to Chicago Flight Information

Avg. Flight Duration 2h 50m
Flights Arrive in Chicago
Flights Depart from Colorado Springs
Flight Price $346
Distance 923 miles
Airlines Frontier, United, Delta, American Airlines

Good to Know

Low Season:
April
Best time to beat the crowds
5%
expected price decrease
High Season:
January
Most popular time to fly
38%
expected price increase
Average Price:
$264
(avg. price over the last 2 weeks)
Good Deal:
$106
or less (round trip)

When to Book Flights from Colorado Springs to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $106 or less.
The cheapest flight from Colorado Springs to Chicago was found 1 day before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Colorado Springs to Chicago Flights

How long does a flight from Colorado Springs to Chicago take?
An average nonstop flight takes 2h 35m, covering a distance of 923 miles.
How many flights are there between Colorado Springs and Chicago?
There are 94 (nonstop) flights between Colorado Springs and Chicago per week, averaging 13 per day.
Which airlines provide the cheapest flights from Colorado Springs to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($346), Frontier ($353) and United ($359).
Do I need a passport to fly between Colorado Springs and Chicago?
No.
Which airlines fly most frequently between Colorado Springs and Chicago?
United (6 times daily), Lufthansa (4 times daily), American Airlines (2 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Colorado Springs to Chicago?
For Colorado Springs to Chicago, Friday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Colorado Springs, the best deals are generally found on Friday, with Saturday being the most expensive.

Book cheap flights from Colorado Springs to Chicago (round-trip)

Airports
Origin
Colorado Springs
$346
only
$346
Destination
Chicago
$346
only
$346
$396
only
$396
Fri, Oct 12
COS
Colorado Springs
ORD
Chicago O'Hare International
11h 16m
Mon, Oct 15
ORD
Chicago O'Hare International
COS
Colorado Springs
15h 21m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Sep 28
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 35m
Wed, Oct 3
ORD
Chicago O'Hare International
COS
Colorado Springs
10h 57m
Trip: 6 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 4 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
DEN
Mediocre 3.3

Nothing

The seats were so in comfortable and made my back hurt

DFW
DEN
Okay 5.0

Sardine-like seating

MCO
PVD
Mediocre 3.2

Total scam. They charge you for every step along the way. Ridiculous hidden fees.

DEN
SNA
Excellent 9.2

FAST BOARDING. NICE AND COLD FLIGHT.

BAD QUALITY COFFEE.

DEN
ALB
Mediocre 2.0

Nothing

Poor food choices, beverage purchaces mandatory, seats do not recline, excessive Frontier credit card sales pitch and most of all, expectation of gratuity for services.

Thu, Nov 1
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 51m
Tue, Nov 6
ORD
Chicago O'Hare International
COS
Colorado Springs
2h 53m
Trip: 6 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 29 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
COS
ORD
Good 6.0

Flights were fine once we got off the ground.

Flight was delayed 6 hours, not due to weather. Really unfortunate that I had to spend an entire day of a long weekend sitting in an airport. Wasn't reimbursed at all for any of the mess, but I guess that is life!

COS
ORD
Excellent 8.0

I am fine with the airline other than a 5 hour delay. I I will never use Kayak again.

COS
ORD
Okay 4.3

Boarding was fast although the flight was delayed 15 minutes. The were very quick and kind.

The seat kept slowly reclining and I had to continually pull the seat up. I paid extra because it was Economy Plus and had extra leg room.

COS
ORD
Mediocre 2.0

My flight was cancelled and I was not notified even though I had signed up for text and email updates.

COS
ORD
Good 6.0

Overall, I was satisfied with my flight experience. There were no delays and boarding was smooth.

I had the same sad flight attendant on both flights that I had that day. Her name was Brittany. She didn't smile or seem at all content to be alive. It was awkward. Also, wish we had wifi.

Thu, Nov 1
COS
Colorado Springs
MDW
Chicago Midway
8h 23m
Tue, Nov 6
MDW
Chicago Midway
COS
Colorado Springs
7h 09m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
FLL
LGA
Good 7.3

Boarding is as usual chaotic

ATL
GPT
Good 6.0

fast flight

Wi-fi sucks

ATL
SJC
Excellent 8.0

Not much food offered on a long flight.

FNT
ATL
Good 6.0

fast flight

Wi-fi sucks

CDG
EWR
Excellent 10.0

Food, comfort, entertainment and treatment by the crew on this flight was spectacular. There was a lot of food, good entertainment and importantly, the seats were wide and comfortable.

Very old plane, 767-300. The bathrooms needed a better and more thorough renovation.

Tue, Jan 1
COS
Colorado Springs
ORD
Chicago O'Hare International
5h 04m
Sun, Jan 6
ORD
Chicago O'Hare International
COS
Colorado Springs
3h 00m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 33,898 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.8
Food
6.7
PHL
MCO
Mediocre 2.0

Beat up baggage

JFK
ORF
Mediocre 3.6

Nice crew

Flight was 55 minutes late leaving making me miss my connection home. Awesome.

MIA
SAT
Excellent 9.6

Great service and on time flight.

Just wish sears would be a bit wider and comfortable. They are not bad but I am sure could be more comfy because I am not skinny.

PHX
DTW
Good 6.6

Flights were always on time . Most staff members were friendly. Seats are comfortable. I looove that they allow you a purse and a true carry on .

Movie selection on long flights not impressive .

LAS
DCA
Good 7.0

Paid for gogoinflight, then is had a big error red screen, that said keep trying back in a few minutes. Never worked. Was not happy. Long flight.

Thu, Dec 13
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 43m
Sun, Dec 16
ORD
Chicago O'Hare International
COS
Colorado Springs
2h 54m
Trip: 4 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 29 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
COS
ORD
Excellent 8.0

I am fine with the airline other than a 5 hour delay. I I will never use Kayak again.

COS
ORD
Good 6.0

Overall, I was satisfied with my flight experience. There were no delays and boarding was smooth.

I had the same sad flight attendant on both flights that I had that day. Her name was Brittany. She didn't smile or seem at all content to be alive. It was awkward. Also, wish we had wifi.

COS
ORD
Excellent 10.0

On time, flight attendants were friendly

COS
ORD
Mediocre 2.0

My flight out of COS was delayed by 3 and a half hours yet my connecting flight was on time. They were unable to get me another connecting flight without me being held up and landing at the wee hours of the morning. It wasn't until I demanded an upgrade from United that I was placed on an American Airlines flight. This would never have been offered if I didn't go off on the representative and demand it. American Airlines saved the day! Never again will I fly United.

Everything.. flight never happened. Upgrade was never offered until I demanded it. The experience was so bad that I will never book with them again. They also still owe me my baggage fee back. That should be interesting.

COS
ORD
Excellent 10.0

Everyone was really nice.

Not enough free food options for active duty flyers.

Thu, Jan 17
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 50m
Sun, Jan 20
ORD
Chicago O'Hare International
COS
Colorado Springs
3h 00m
Trip: 4 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 29 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
COS
ORD
Okay 4.3

Boarding was fast although the flight was delayed 15 minutes. The were very quick and kind.

The seat kept slowly reclining and I had to continually pull the seat up. I paid extra because it was Economy Plus and had extra leg room.

COS
ORD
Excellent 10.0

On time, flight attendants were friendly

COS
ORD
Mediocre 2.0

My flight was cancelled and I was not notified even though I had signed up for text and email updates.

COS
ORD
Excellent 8.0

Bosrding, seating comfortable and timely. Would appreciate a small snack with beverage

COS
ORD
Excellent 10.0

Everyone was really nice.

Not enough free food options for active duty flyers.

Wed, Nov 21
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 51m
Tue, Nov 27
ORD
Chicago O'Hare International
COS
Colorado Springs
2h 53m
Trip: 7 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 29 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
COS
ORD
Excellent 8.0

I am fine with the airline other than a 5 hour delay. I I will never use Kayak again.

COS
ORD
Mediocre 2.0

My flight out of COS was delayed by 3 and a half hours yet my connecting flight was on time. They were unable to get me another connecting flight without me being held up and landing at the wee hours of the morning. It wasn't until I demanded an upgrade from United that I was placed on an American Airlines flight. This would never have been offered if I didn't go off on the representative and demand it. American Airlines saved the day! Never again will I fly United.

Everything.. flight never happened. Upgrade was never offered until I demanded it. The experience was so bad that I will never book with them again. They also still owe me my baggage fee back. That should be interesting.

COS
ORD
Good 6.0

Overall, I was satisfied with my flight experience. There were no delays and boarding was smooth.

I had the same sad flight attendant on both flights that I had that day. Her name was Brittany. She didn't smile or seem at all content to be alive. It was awkward. Also, wish we had wifi.

COS
ORD
Excellent 10.0

The planes weren’t overly packed and everyplane was on time

None

COS
ORD
Excellent 10.0

Everyone was really nice.

Not enough free food options for active duty flyers.

Fri, Oct 19
COS
Colorado Springs
MDW
Chicago Midway
8h 23m
Mon, Oct 22
MDW
Chicago Midway
COS
Colorado Springs
6h 02m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
SJC
Excellent 8.0

Not much food offered on a long flight.

BRU
ATL
Excellent 9.3

The check in was well staffed and went smoothly and easily. Loved the large movie selection and picture quality.

CDG
EWR
Excellent 10.0

Food, comfort, entertainment and treatment by the crew on this flight was spectacular. There was a lot of food, good entertainment and importantly, the seats were wide and comfortable.

Very old plane, 767-300. The bathrooms needed a better and more thorough renovation.

ROC
ATL
Excellent 10.0

Marti

CDG
IND
Good 7.3

The service on our flight was absolutely amazing, the food was surprisingly great, and the long ride was as comfortable as it could have been in an economy booking.

My entertainment pad malfunctioned the whole time, even after it was reset. Thankfully I had enough things to keep me busy on my own, but it still would have been nice to have.

Fri, Mar 8
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 41m
Mon, Mar 11
ORD
Chicago O'Hare International
COS
Colorado Springs
12h 50m
Trip: 3 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 29 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
COS
ORD
Excellent 10.0

The planes weren’t overly packed and everyplane was on time

None

COS
ORD
Okay 4.3

Boarding was fast although the flight was delayed 15 minutes. The were very quick and kind.

The seat kept slowly reclining and I had to continually pull the seat up. I paid extra because it was Economy Plus and had extra leg room.

COS
ORD
Excellent 8.0

I am fine with the airline other than a 5 hour delay. I I will never use Kayak again.

COS
ORD
Good 6.0

Flights were fine once we got off the ground.

Flight was delayed 6 hours, not due to weather. Really unfortunate that I had to spend an entire day of a long weekend sitting in an airport. Wasn't reimbursed at all for any of the mess, but I guess that is life!

COS
ORD
Good 6.3

I typically dont fly with united, and this was a typical experience, staff was not friendly, terminal and gate change at last minute after I walking all the way to the gate, then another delay after we were boarded, now this was more airport related then United, but after they told us it was a 45min delay someone asked if we can use our phone or computer and the answer was a stern no with no explanation until someone got really upset, just not a professional experience, and this was why I don't fly united. But I had no choice this time.

Thu, Dec 13
COS
Colorado Springs
MDW
Chicago Midway
7h 16m
Sun, Dec 16
MDW
Chicago Midway
COS
Colorado Springs
7h 35m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
DCA
Good 7.3

There was no rhyme nor reason for who boarded first

BRU
ATL
Excellent 9.3

The check in was well staffed and went smoothly and easily. Loved the large movie selection and picture quality.

FLL
LGA
Good 7.3

Boarding is as usual chaotic

ICN
ATL
Okay 4.3

Free movies available in-flight

temperature during flight. Freezing then hot, freezing then hot and never a comfortable temp. Food was terrible. Entrees were flavorless and smelled terrible. Time they served food made no sense at all either. Within the hour of getting on the plane, they served a meal which made no sense because most folks ate before getting on the plane. Stewardesses were not friendly (only 1 made me feel valued and welcomed)

CDG
IND
Good 7.3

The service on our flight was absolutely amazing, the food was surprisingly great, and the long ride was as comfortable as it could have been in an economy booking.

My entertainment pad malfunctioned the whole time, even after it was reset. Thankfully I had enough things to keep me busy on my own, but it still would have been nice to have.

Thu, Oct 4
COS
Colorado Springs
ORD
Chicago O'Hare International
2h 40m
Mon, Oct 8
ORD
Chicago O'Hare International
COS
Colorado Springs
2h 45m
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 29 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
COS
ORD
Mediocre 2.0

My flight was cancelled and I was not notified even though I had signed up for text and email updates.

COS
ORD
Excellent 8.0

Seating was nice, middle seat was empty

I landed at F1 and had to run to C29. No time to even grab a snack!

COS
ORD
Excellent 8.0

I am fine with the airline other than a 5 hour delay. I I will never use Kayak again.

COS
ORD
Good 6.3

I typically dont fly with united, and this was a typical experience, staff was not friendly, terminal and gate change at last minute after I walking all the way to the gate, then another delay after we were boarded, now this was more airport related then United, but after they told us it was a 45min delay someone asked if we can use our phone or computer and the answer was a stern no with no explanation until someone got really upset, just not a professional experience, and this was why I don't fly united. But I had no choice this time.

COS
ORD
Excellent 10.0

Everyone was really nice.

Not enough free food options for active duty flyers.

Sat, Nov 10
COS
Colorado Springs
MDW
Chicago Midway
8h 15m
Tue, Nov 20
MDW
Chicago Midway
COS
Colorado Springs
10h 42m
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
SJC
Excellent 8.0

Not much food offered on a long flight.

CDG
EWR
Excellent 10.0

Food, comfort, entertainment and treatment by the crew on this flight was spectacular. There was a lot of food, good entertainment and importantly, the seats were wide and comfortable.

Very old plane, 767-300. The bathrooms needed a better and more thorough renovation.

ATL
ORF
Okay 4.6

Free movies available in flight

Airplane temp never comfortable Airline staff not friendly Wheelchair service terrible

FLL
LGA
Good 7.3

Boarding is as usual chaotic

CDG
IND
Good 7.3

The service on our flight was absolutely amazing, the food was surprisingly great, and the long ride was as comfortable as it could have been in an economy booking.

My entertainment pad malfunctioned the whole time, even after it was reset. Thankfully I had enough things to keep me busy on my own, but it still would have been nice to have.

Fri, Mar 8
COS
Colorado Springs
MDW
Chicago Midway
7h 34m
Mon, Mar 11
MDW
Chicago Midway
COS
Colorado Springs
7h 42m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
CDG
IND
Good 7.3

The service on our flight was absolutely amazing, the food was surprisingly great, and the long ride was as comfortable as it could have been in an economy booking.

My entertainment pad malfunctioned the whole time, even after it was reset. Thankfully I had enough things to keep me busy on my own, but it still would have been nice to have.

ATL
ORF
Okay 4.6

Free movies available in flight

Airplane temp never comfortable Airline staff not friendly Wheelchair service terrible

FNT
ATL
Good 6.0

fast flight

Wi-fi sucks

LGA
DCA
Good 7.3

There was no rhyme nor reason for who boarded first

ICN
ATL
Okay 4.3

Free movies available in-flight

temperature during flight. Freezing then hot, freezing then hot and never a comfortable temp. Food was terrible. Entrees were flavorless and smelled terrible. Time they served food made no sense at all either. Within the hour of getting on the plane, they served a meal which made no sense because most folks ate before getting on the plane. Stewardesses were not friendly (only 1 made me feel valued and welcomed)

Sat, Sep 29
COS
Colorado Springs
MDW
Chicago Midway
5h 14m
Tue, Oct 16
MDW
Chicago Midway
COS
Colorado Springs
12h 45m
Trip: 18 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
FNT
ATL
Good 6.0

fast flight

Wi-fi sucks

FLL
LGA
Good 7.3

Boarding is as usual chaotic

BRU
ATL
Excellent 9.3

The check in was well staffed and went smoothly and easily. Loved the large movie selection and picture quality.

ATL
SJC
Excellent 8.0

Not much food offered on a long flight.

ATL
GPT
Good 6.0

fast flight

Wi-fi sucks

Mon, Dec 24
COS
Colorado Springs
ORD
Chicago O'Hare International
6h 33m
Wed, Jan 2
ORD
Chicago O'Hare International
COS
Colorado Springs
9h 55m
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,439 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ROC
ATL
Excellent 10.0

Marti

FLL
LGA
Good 7.3

Boarding is as usual chaotic

BRU
ATL
Excellent 9.3

The check in was well staffed and went smoothly and easily. Loved the large movie selection and picture quality.

LGA
DCA
Good 7.3

There was no rhyme nor reason for who boarded first

ICN
ATL
Okay 4.3

Free movies available in-flight

temperature during flight. Freezing then hot, freezing then hot and never a comfortable temp. Food was terrible. Entrees were flavorless and smelled terrible. Time they served food made no sense at all either. Within the hour of getting on the plane, they served a meal which made no sense because most folks ate before getting on the plane. Stewardesses were not friendly (only 1 made me feel valued and welcomed)

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