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

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Wed 12/13
Wed 12/20
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Looking for a cheap flight? 25% of our users found flights on this route for $188 or less.

FAQs for Booking Colorado Springs to Chicago Midway Flights

How long does a flight from Colorado Springs to Chicago Midway take?
An average nonstop flight takes 7h 59m, covering a distance of 916 miles.
Which airlines provide the cheapest flights from Colorado Springs to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($376)
Do I need a passport to fly between Colorado Springs and Chicago Midway?
No.
What’s the cheapest day of the week to fly Colorado Springs to Chicago Midway?
For Colorado Springs to Chicago Midway, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago Midway back to Colorado Springs, the best deals are generally found on Thursday, with Tuesday being the most expensive.

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

Airports
Origin
Colorado Springs
$376
only
$376
Destination
Chicago
$376
only
$376
Fri, Jan 26
COS
MDW
8h 10m
Tue, Jan 30
MDW
COS
10h 46m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
LAX
Excellent 10.0

Excellent service and upgraded snacks in economy

Nothing

LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

LGA
DFW
Excellent 10.0

On time with no drama

LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

Sat, Apr 14
COS
MDW
7h 59m
Sat, Apr 21
MDW
COS
8h 56m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LHR
JFK
Good 7.0

Delays!

SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

SJC
LAX
Mediocre 2.0

They were very dishonest about everything. We need to be there in Australia on Monday morning for very important event but reached Australia Monday night 8PM. Virgin Australia contatcted out their flight from SJC to LAX through Delta and Delta cancelled flights becaue no-show of Pilot to operate the plan. What a Joke???? We asked them to put us through another carrier to LAX for connecting flight they refused.Very very BAD. It was a big miss for us.. never again Delta/Virgin Australia..............

LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

Thu, Feb 15
COS
MDW
8h 10m
Mon, Feb 19
MDW
COS
9h 15m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

LGA
DFW
Excellent 10.0

On time with no drama

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

Fri, Mar 16
COS
MDW
8h 00m
Sun, Mar 18
MDW
COS
9h 01m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

LHR
JFK
Good 7.0

Delays!

SJC
LAX
Mediocre 2.0

They were very dishonest about everything. We need to be there in Australia on Monday morning for very important event but reached Australia Monday night 8PM. Virgin Australia contatcted out their flight from SJC to LAX through Delta and Delta cancelled flights becaue no-show of Pilot to operate the plan. What a Joke???? We asked them to put us through another carrier to LAX for connecting flight they refused.Very very BAD. It was a big miss for us.. never again Delta/Virgin Australia..............

ATL
MEX
Excellent 8.6

Sandwich for dinner

Thu, Dec 14
COS
MDW
8h 45m
Mon, Dec 18
MDW
COS
8h 17m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

LGA
DFW
Excellent 10.0

On time with no drama

SJC
LAX
Mediocre 2.0

They were very dishonest about everything. We need to be there in Australia on Monday morning for very important event but reached Australia Monday night 8PM. Virgin Australia contatcted out their flight from SJC to LAX through Delta and Delta cancelled flights becaue no-show of Pilot to operate the plan. What a Joke???? We asked them to put us through another carrier to LAX for connecting flight they refused.Very very BAD. It was a big miss for us.. never again Delta/Virgin Australia..............

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.