$39 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 7/5. 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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Flights Deals

Best Colorado Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Denver
Denver1 stop$94
Aspen
Aspen1 stop$609
Grand Junction
Grand Junction2 stops$304
Denver
Denver1 stop$94
Aspen
Aspen1 stop$609
Grand Junction
Grand Junction2 stops$304

Cheap Flights from Midway to Colorado

 
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.

Recent round-trip flight deals from Midway to Colorado

Tue, Jul 29 - Mon, Aug 4
Frontier Logo
11:39 am - 9:17 pmMDW-DEN
10h 38m1 stop
Frontier Logo
8:15 am - 11:41 amDEN-MDW
2h 26mnonstop
$94Frontier
Find Deal
Thu, Jul 24 - Sat, Jul 26
Frontier Logo
2:44 pm - 4:33 pmMDW-DEN
2h 49mnonstop
Frontier Logo
5:26 pm - 8:54 pmDEN-MDW
2h 28mnonstop
$97Frontier
Find Deal
Fri, Jul 18 - Mon, Jul 21
Frontier Logo
12:35 pm - 2:19 pmMDW-DEN
2h 44mnonstop
Frontier Logo
8:15 am - 11:41 amDEN-MDW
2h 26mnonstop
$98Frontier
Find Deal
Thu, Jul 17 - Mon, Jul 21
Frontier Logo
2:44 pm - 4:33 pmMDW-DEN
2h 49mnonstop
Frontier Logo
8:15 am - 11:41 amDEN-MDW
2h 26mnonstop
$99Frontier
Find Deal
Mon, Aug 11 - Tue, Aug 19
Southwest Logo
7:45 am - 9:10 amMDW-COS
2h 25mnonstop
Southwest Logo
11:55 am - 3:15 pmCOS-MDW
2h 20mnonstop
$197Southwest
Find Deal
Mon, Aug 11 - Tue, Aug 19
Southwest Logo
7:45 am - 9:10 amMDW-COS
2h 25mnonstop
Southwest Logo
6:00 am - 3:45 pmCOS-MDW
8h 45m1 stop
$199Southwest
Find Deal
Mon, Aug 11 - Tue, Aug 19
Southwest Logo
7:45 am - 9:10 amMDW-COS
2h 25mnonstop
Southwest Logo
6:45 am - 2:30 pmCOS-MDW
6h 45m2 stops
$204Southwest
Find Deal
Mon, Aug 11 - Mon, Aug 18
Delta Logo
12:43 pm - 8:41 pmMDW-COS
8h 58m1 stop
Delta Logo
11:06 am - 5:37 pmCOS-MDW
5h 31m1 stop
$217Delta
Find Deal
Tue, Aug 12 - Tue, Aug 19
Delta Logo
1:08 pm - 8:41 pmMDW-COS
8h 33m2 stops
Delta Logo
11:06 am - 5:37 pmCOS-MDW
5h 31m1 stop
$222Delta
Find Deal
Sat, Aug 16 - Tue, Aug 19
Delta Logo
9:31 am - 8:41 pmMDW-COS
12h 10m2 stops
Delta Logo
1:10 pm - 9:44 pmCOS-MDW
7h 34m1 stop
$238Delta
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Colorado.

The cheapest ticket to Colorado from Chicago Midway Airport found in the last 72 hours was to Denver, at $144 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 $144.

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 $272, 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 $152 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $218 and $212 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 Saturday 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 Saturdays 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. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonApril
High seasonOctober
Cheapest flight$39
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 1% increase in price.
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 $189 on average. Morning departures are around 15% 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 $222.

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 $125 one-way - $184 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 4278 reviews
7.0Food
7.6Entertainment
8.2Boarding
8.6Crew
8.0Comfort
Airline reviews

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

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

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.

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

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.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

The plane failed preflight inspection, so we sat there for 90 mins while they tried to fix it. Ultimately, everything was remedied and we made our connecting flight; instead of a 2 hour layover at the airport, we spent it waiting on the plane.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Delayed each time on a round trip with no significant weather interference. Updates to flight times came after the fact. 30 min behind in boarding and board and phone still show an on time departure. Some mysterious extra 300 miles that came so surprising they had to fuel while we were already on board?

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

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

Information on your arrival and departure airports

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