MDW - DEN

$108 Find Cheap Flights from Chicago Midway Airport to Denver - 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 Denver departing on 7/25. 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 Denver

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Denver, 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 Denver, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$205
Typical prices: $190-$323
Southwest
Wed 8/12Wed 8/19
MDW - DEN • Non-stop
Cheapest one-way
$108
Typical prices: $104-$258
Southwest
Sat 7/25
MDW - DEN • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier Economy Bundle adds a carry-on and seat selection for budget value.
Southwest Rapid Rewards has no blackout dates; free snacks add extra value.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $205 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 38m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Avoid delays
Most punctual • 78% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $190 (round-trip)
Shortest trip • 5h 43m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 38% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights from Midway to Denver (MDW-DEN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Denver 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 Denver

Wed, Aug 12 - Wed, Aug 19
Southwest Logo
6:40 am - 8:10 am
MDW
-
DEN
2h 30mnonstop
Southwest Logo
7:25 pm - 10:50 pm
DEN
-
MDW
2h 25mnonstop
$205Southwest
Thu, Aug 13 - Sat, Aug 15
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
Southwest Logo
6:00 am - 9:20 am
DEN
-
MDW
2h 20mnonstop
$206Southwest
Mon, Aug 10 - Mon, Aug 17
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
Southwest Logo
6:30 pm - 10:00 pm
DEN
-
MDW
2h 30mnonstop
$208Southwest
Wed, Aug 12 - Wed, Aug 19
Frontier Logo
4:45 pm - 10:55 pm
MDW
-
DEN
7h 10m
1 stop
Frontier Logo
10:43 am - 10:47 pm
DEN
-
MDW
11h 04m
1 stop
$210Frontier
Sat, Aug 1 - Sat, Aug 15
Southwest Logo
10:15 am - 1:20 pm
MDW
-
DEN
4h 05m
1 stop
Southwest Logo
6:00 am - 9:20 am
DEN
-
MDW
2h 20mnonstop
$211Southwest
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
5:00 pm - 7:50 pm
MDW
-
DEN
3h 50m
1 stop
Southwest Logo
6:30 am - 9:50 am
DEN
-
MDW
2h 20mnonstop
$212Southwest
Mon, Aug 10 - Mon, Aug 17
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
Southwest Logo
3:15 pm - 7:45 pm
DEN
-
MDW
3h 30m
1 stop
$213Southwest
Wed, Jul 22 - Sat, Jul 25
Southwest Logo
7:40 am - 11:45 am
MDW
-
DEN
5h 05m
1 stop
Southwest Logo
5:15 am - 8:35 am
DEN
-
MDW
2h 20mnonstop
$215Southwest
Sat, Aug 1 - Sat, Aug 15
Southwest Logo
10:15 am - 1:20 pm
MDW
-
DEN
4h 05m
1 stop
Southwest Logo
11:10 am - 5:10 pm
DEN
-
MDW
5h 00m
1 stop
$216Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
9:00 am - 12:55 pm
MDW
-
DEN
4h 55m
1 stop
Southwest Logo
11:10 am - 5:10 pm
DEN
-
MDW
5h 00m
1 stop
$217Southwest
Booking Insights

KAYAK's insights & trends for Midway to Denver flights

Get data-powered insights and trends into flights from Midway to Denver 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 Denver?

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 Denver departing in August.

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

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

If your flying dates are flexible, you should consider flying to Denver on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Denver. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

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

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 Denver, 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 Denver is October, where tickets cost $173 (return) on average. On the other hand, the most expensive months are June and April, where the average cost of round-trip tickets is $364 and $339 respectively.

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

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 $327, prices are generally cheapest when you fly direct.

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

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 Denver, 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 Denver, you should book around 3 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Expert advice

Expert advice for your flight from Midway to Denver

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on DEN

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Good to know

Low seasonJanuary
Cheapest flight$108
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Chicago Midway Airport to Denver

When to book flights from Midway to Denver

Are your dates flexible? Find out the best times to travel from Midway to Denver based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Denver flights

  • Which airlines have well-suited services for business travelers from Chicago Midway Airport to Denver?

    Business travelers should consider flying with United or Delta Air Lines for their flights to Denver. United Airlines offers premium seating options, including the United Polaris business class. It has power outlets at every seat, allowing business travelers to stay charged and connected while on board. Delta Air Lines offers noise-canceling headphones that block out noise.

  • Which airlines from Chicago Midway Airport-Denver are environmentally-friendly?

    Delta Air Lines is a worthy choice for environmentally-conscious travelers from MDW to Denver. It engages its employees in sustainability initiatives such as recycling and waste reduction programs. It sources sustainable products like certified seafood and coffee, and has implemented water conservation initiatives such as low-flow faucets and toilets to reduce water consumption.

  • What flight alliances are there for flights from Chicago Midway Airport to Denver?

    OneWorld and SkyTeam are flight alliances that operate flights from MDW to Denver. American Airlines, a member of OneWorld, allows travelers to book and manage their travel across multiple airlines, making the trip convenient. SkyTeams member Delta Air Lines reduces costs by sharing resources and coordinating schedules.

  • Does Delta Air Lines offer special meals to its passengers?

    Delta Air Lines offers different types of dietary meals for travelers on board. They offer lactose-free and kosher meals. Passengers on board also get Vegan and gluten-free meals. Passengers request these special meals when booking their flight or contacting Delta Customer Service.

  • What is the cheapest flight from Chicago Midway Airport to Denver?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Denver was $108 for a one-way ticket and $205 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Denver?

    No, a passport isn't needed to fly from Chicago Midway Airport to Denver. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Denver?

    On your way to Denver, you’ll fly out from Chicago Midway. You’ll be landing at Denver Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Denver?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to Denver flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Denver?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Denver flight route.

  • On which days can I fly direct from Chicago Midway Airport to Denver?

    There are nonstop flights from Chicago Midway Airport to Denver on a daily basis.

  • Which is the best airline for flights from Chicago to Denver, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Denver are Southwest and Frontier. With an average price for the route of $297 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $180 and an overall rating of 5.6.

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

    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 Denver.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Denver from Chicago Midway Airport 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 Denver?

    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 to Denver with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and DEN can sometimes prove cheaper using this method.

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

    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 to Denver from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Denver

  • Looking for a cheap flight? 25% of our users found flights on this route for $195 or less one-way and $293 or less round-trip.
  • Delta Air Lines offer various class tickets to its passengers. Basic Economy is Delta's most basic fare class, a low-cost option. Main Cabin is Delta's standard economy class that includes snacks and drinks. Delta's premium economy class, Delta Comfort+, offers extra legroom. First Class provides wider seats, while Delta One, the highest rank, offers personalized service and lie-flat seats.
  • Southwest Airlines enables non-elite members to upgrade to first class by purchasing an upgrade with cash or points up to 36 hours before the flight. They can also bid for an upgrade or join the Rapid Rewards Program, earning them points towards the Business Select Ticket and an upgrade. Elite members also have to pay for an upgrade up to 72 hours before their flight.
  • Frontier Airlines offers layover stops at Miami International Airport (MIA) and Hartsfield-Jackson Atlanta International Airport (ATL). Delta Air Lines has layovers at Minneapolis-Saint Paul International Airport (MSP) that last for about 98 minutes, and another at Detroit Metropolitan Wayne County Airport (DTW).
  • Delta Air Lines takes good care of minors traveling from Chicago Midway Airport (MDW) to Denver (DEN). They provide a special seat for the minor and snacks and drinks during the flight. They monitor the minors on board and check on them periodically. Before the minor boards the flight, Delta Air Lines ensures they have the necessary documentation for the flight.
  • Frontier Airlines is a good option for travelers on a tight budget from Chicago Midway Airport to Denver. It has a discount program, Discount Den, that provides access to low fares and other perks. It offers fare sales that save you money on flights. Frontier Airlines regularly flies to secondary airports, which are less expensive than major airports.

Prefer to fly direct from Chicago Midway Airport to Denver?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Denver Intl.
Find which airlines fly direct from Chicago Midway Airport to Denver Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Denver Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Denver Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

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Sunday

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See more direct flights

Reviews of the top airlines flying from Midway to Denver

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Denver. 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 Denver? 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 4246 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
CMH - DEN
Read more Southwest reviews

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

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.

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 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.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

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...

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!

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Long delay due to mechanical issues. They should have just swapped the plane and not make us wait while they figure it out. Disappointed

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!!!

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.

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!!!

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

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.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

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

Information on your arrival and departure airports