$103 Find Cheap Flights from Chicago Midway Airport to Colorado - Compare and Save

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 8/11. 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, 0 bags

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
Denver2 stops$176
Colorado Springs
Colorado Springsnonstop$241
Aspen
Aspen1 stop$421
Grand Junction
Grand Junction2 stops$309
Denver
Denver2 stops$176
Colorado Springs
Colorado Springsnonstop$241
Aspen
Aspen1 stop$421
Grand Junction
Grand Junction2 stops$309

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.

Recent round-trip flight deals from Midway to Colorado

Tue, Aug 11 - Wed, Aug 12
Southwest Logo
1:55 pm - 7:50 pm
MDW
-
DEN
6h 55m
2 stops
Southwest Logo
1:55 pm - 7:25 pm
DEN
-
MDW
4h 30m
1 stop
$176Southwest
Tue, Aug 11 - Thu, Aug 13
Southwest Logo
6:40 am - 8:10 am
MDW
-
DEN
2h 30mnonstop
Southwest Logo
4:55 pm - 8:15 pm
DEN
-
MDW
2h 20mnonstop
$183Southwest
Wed, Jul 29 - Tue, Aug 4
Southwest Logo
7:00 am - 8:35 am
MDW
-
DEN
2h 35mnonstop
Southwest Logo
11:15 am - 5:00 pm
DEN
-
MDW
4h 45m
1 stop
$188Southwest
Wed, Aug 5 - Mon, Aug 10
Southwest Logo
8:55 am - 12:55 pm
MDW
-
DEN
5h 00m
1 stop
Southwest Logo
8:25 pm - 11:45 pm
DEN
-
MDW
2h 20mnonstop
$189Southwest
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
10:05 am - 2:25 pm
MDW
-
DEN
5h 20m
1 stop
Southwest Logo
6:30 am - 9:50 am
DEN
-
MDW
2h 20mnonstop
$193Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
2:15 pm - 6:30 pm
MDW
-
DEN
5h 15m
1 stop
Southwest Logo
11:15 am - 5:00 pm
DEN
-
MDW
4h 45m
1 stop
$194Southwest
Wed, Aug 5 - Mon, Aug 10
Southwest Logo
8:55 am - 12:55 pm
MDW
-
DEN
5h 00m
1 stop
Southwest Logo
6:25 am - 12:15 pm
DEN
-
MDW
4h 50m
1 stop
$198Southwest
Wed, Aug 26 - Fri, Aug 28
Southwest Logo
8:50 pm - 10:25 pm
MDW
-
DEN
2h 35mnonstop
Southwest Logo
6:30 pm - 10:00 pm
DEN
-
MDW
2h 30mnonstop
$201Southwest
Tue, Aug 11 - Fri, Aug 14
Delta Logo
7:25 pm - 11:34 pm
MDW
-
DEN
5h 09m
1 stop
Delta Logo
12:59 am - 9:17 am
DEN
-
MDW
7h 18m
1 stop
$204Delta
Sat, Oct 24 - Tue, Oct 27
Delta Logo
9:30 am - 5:14 pm
MDW
-
COS
8h 44m
2 stops
Delta Logo
5:55 pm - 9:52 am
COS
-
MDW
14h 57m
2 stops
$277Delta
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.

How much is a round-trip flight from Chicago Midway Airport to Colorado?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Colorado departing in August.

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 5 days was to Denver, at $241 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 5 days was $241.

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

The average price for all round-trip flights from Chicago Midway Airport to Colorado depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Colorado is generally in the afternoon, when round-trip flights cost $244 on average. Morning departures are around 17% more expensive than evening flights, on average. The most expensive time of day to fly to Colorado is generally in the morning, which is peak travel time and where the average cost of a ticket is $292.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $366 on average.

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 $62 (return) on average. On the other hand, the most expensive months are April and February, when the average cost of round-trip tickets is $201 and $185 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 Thursday 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 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$103
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 20% 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.

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 $178 one-way - $278 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.
7.9
SouthwestOverall score based on 4237 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

It was an early flight and most people napped/slept and the crew let us which was nice.

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Better than expected. Staff were friendly and nice on both flights.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

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

Information on your arrival and departure airports