$53 Find Cheap Flights from Chicago Midway Airport to Colorado

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Colorado departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Colorado

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Colorado, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Colorado, as well as popular online travel agencies
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Cheap Flights from Midway to Colorado

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Denver
Denvernonstop$104
Aspen
Aspen1 stop$408
Grand Junction
Grand Junction2 stops$775
Denver
Denvernonstop$104
Aspen
Aspen1 stop$408
Grand Junction
Grand Junction2 stops$775

Book Cheap Midway to Colorado Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Colorado that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Colorado

Fri, Sep 5 - Mon, Sep 8
Frontier Logo
4:48 pm - 6:26 pmMDW-DEN
2h 38mnonstop
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
$104Frontier
Find Deal
Fri, Oct 10 - Thu, Oct 16
Frontier Logo
6:24 pm - 8:08 pmMDW-DEN
2h 44mnonstop
Frontier Logo
9:12 pm - 12:36 amDEN-MDW
2h 24mnonstop
$105Frontier
Find Deal
Fri, Sep 19 - Mon, Sep 22
Frontier Logo
3:48 pm - 5:32 pmMDW-DEN
2h 44mnonstop
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
$107Frontier
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
6:24 pm - 8:08 pmMDW-DEN
2h 44mnonstop
Frontier Logo
9:12 pm - 12:36 amDEN-MDW
2h 24mnonstop
$108Frontier
Find Deal
Tue, Sep 30 - Tue, Oct 7
Southwest Logo
3:50 pm - 5:20 pmMDW-DEN
2h 30mnonstop
Southwest Logo
7:15 am - 10:35 amDEN-MDW
2h 20mnonstop
$137Southwest
Find Deal
Tue, Sep 30 - Thu, Oct 2
Southwest Logo
12:10 pm - 1:45 pmMDW-DEN
2h 35mnonstop
Southwest Logo
8:15 pm - 11:30 pmDEN-MDW
2h 15mnonstop
$147Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
9:00 am - 10:35 amMDW-DEN
2h 35mnonstop
Southwest Logo
5:20 pm - 8:40 pmDEN-MDW
2h 20mnonstop
$157Southwest
Find Deal
Tue, Sep 2 - Tue, Sep 9
Delta Logo
9:15 am - 5:15 pmMDW-COS
9h 00m2 stops
Delta Logo
1:10 pm - 9:26 pmCOS-MDW
7h 16m1 stop
$238Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
Delta Logo
9:35 am - 8:39 pmMDW-COS
12h 04m2 stops
Delta Logo
1:11 pm - 9:36 pmCOS-MDW
7h 25m1 stop
$248Delta
Find Deal
Sat, Sep 13 - Tue, Sep 16
Delta Logo
9:35 am - 8:39 pmMDW-COS
12h 04m2 stops
Delta Logo
1:11 pm - 9:36 pmCOS-MDW
7h 25m1 stop
$273Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Colorado flights

Get data-powered insights and trends into flights from Midway to Colorado to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Colorado flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Colorado from Chicago Midway Airport found in the last 72 hours was to Denver, at $108 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Denver (DEN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $108.

Can I save money by flying with a layover from Chicago Midway Airport to Colorado?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $224, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Colorado?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Colorado, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Colorado is November, when tickets cost $163 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $238 and $218 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Colorado?

The average price of all round-trip flights from Chicago Midway Airport to Colorado clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Colorado, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

How far in advance should I book a flight from Chicago Midway Airport to Colorado?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Colorado, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Colorado, you should book around 3 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$53
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Chicago Midway Airport to Denver

FAQs - booking Colorado flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Colorado?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Colorado.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Colorado?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Colorado is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Colorado?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Colorado with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Colorado?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Colorado up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Colorado?

    The cheapest time of day to fly to Colorado is generally in the morning, when round-trip flights cost $194 on average. Morning departures are around 11% cheaper than evening flights, on average. The most expensive time of day to fly to Colorado is generally in the evening, which is peak travel time and where the average cost of a ticket is $217.

Top tips for finding cheap flights to Colorado

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Denver $99 one-way - $160 round-trip

Reviews of the top airlines flying from Midway to Colorado

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Colorado. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Colorado? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4244 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Everything you need to know for your flight from Midway to Colorado

Information on your arrival and departure airports

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