DEN - MDW

$90 Find Cheap Flights from Denver to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Denver to Midway departing on 4/28. 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 Chicago Midway Airport

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

Cheapest round-trip
$178
Overall average: $255
Frontier
Tue 5/5Tue 5/12
DEN - MDW • 1 stop
Cheapest non-stop
$201
Typical prices: $180-$276
Southwest
Tue 4/14Tue 4/21
DEN - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags save on luggage fees.
Use the West Security Checkpoint at DEN for faster screening.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $178 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 21m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $228 (round-trip)
Shortest trip • 6h 11m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 41% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Denver to Midway (DEN-MDW)

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

Tue, May 5 - Tue, May 12
Frontier Logo
5:00 pm - 2:12 pm
DEN
-
MDW
20h 12m
1 stop
Frontier Logo
3:07 pm - 6:33 am
MDW
-
DEN
16h 26m
1 stop
$178Frontier
Wed, May 6 - Wed, May 13
Frontier Logo
5:05 am - 2:12 pm
DEN
-
MDW
8h 07m
1 stop
Frontier Logo
12:04 pm - 10:24 pm
MDW
-
DEN
11h 20m
1 stop
$179Frontier
Sat, Apr 18 - Wed, Apr 22
Frontier Logo
1:09 pm - 10:14 pm
DEN
-
MDW
8h 05m
1 stop
Frontier Logo
6:15 am - 12:09 pm
MDW
-
DEN
6h 54m
1 stop
$180Frontier
Mon, May 11 - Thu, May 14
Frontier Logo
11:54 pm - 11:12 am
DEN
-
MDW
10h 18m
1 stop
Frontier Logo
3:07 pm - 8:43 pm
MDW
-
DEN
6h 36m
1 stop
$181Frontier
Wed, Apr 15 - Wed, Apr 22
Frontier Logo
11:59 pm - 7:31 pm
DEN
-
MDW
18h 32m
1 stop
Frontier Logo
2:15 pm - 10:29 pm
MDW
-
DEN
9h 14m
1 stop
$184Frontier
Fri, Apr 17 - Tue, Apr 21
Frontier Logo
6:30 am - 2:34 pm
DEN
-
MDW
7h 04m
1 stop
Frontier Logo
6:10 am - 12:14 pm
MDW
-
DEN
7h 04m
1 stop
$185Frontier
Tue, May 12 - Fri, May 15
Frontier Logo
7:00 am - 2:12 pm
DEN
-
MDW
6h 12m
1 stop
Frontier Logo
3:07 pm - 11:48 pm
MDW
-
DEN
9h 41m
1 stop
$186Frontier
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
11:59 pm - 7:26 am
DEN
-
MDW
30h 27m
1 stop
Frontier Logo
2:15 pm - 10:29 pm
MDW
-
DEN
9h 14m
1 stop
$187Frontier
Fri, Apr 17 - Fri, Apr 24
Frontier Logo
6:30 am - 2:34 pm
DEN
-
MDW
7h 04m
1 stop
Frontier Logo
1:30 pm - 12:20 am
MDW
-
DEN
11h 50m
1 stop
$188Frontier
Wed, May 13 - Sat, May 16
Frontier Logo
5:05 am - 2:12 pm
DEN
-
MDW
8h 07m
1 stop
Frontier Logo
3:07 pm - 11:48 pm
MDW
-
DEN
9h 41m
1 stop
$190Frontier
Booking Insights

KAYAK's insights & trends for Denver to Midway flights

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

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

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

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Friday and more expensive on a Sunday. On your return trip to Denver, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Denver to Chicago Midway Airport, 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 Denver to Chicago Midway Airport is September, where tickets cost $177 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $341 and $307 respectively.

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

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 1 stop layover the cheapest option at $325 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Denver to Chicago Midway Airport, 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 Denver to Chicago Midway Airport, you should book around 4 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Expert advice

Expert advice for your flight from Denver to Midway

 
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$90
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Denver to Chicago Midway Airport

When to book flights from Denver to Midway

Are your dates flexible? Find out the best times to travel from Denver to Midway 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 Denver to Chicago Midway Airport flights

  • What seat selection options are available on Southwest flights from Denver to Chicago Midway Airport?

    On Southwest Airlines flights from Denver to Chicago Midway Airport, seat selection options are based on the airline's open seating policy, also known as “Aisle or Window” seating. Unlike other airlines, Southwest does not assign specific seats to passengers. Instead, passengers are assigned a boarding group (A, B, or C), and within each group, a boarding position number (1-60).

  • What services does Delta offer economy passengers on flights from Denver to Chicago Midway Airport?

    Delta provides personal seat-back screens to every passenger where they can access a wide selection of movies, TV shows, music, and games. The airline offers Wi-Fi connectivity on flights from Denver to Chicago Midway Airport for a fee, and passengers can choose from different packages depending on their need for connections.

  • What is the luggage allowance on Frontier flights from Denver to Chicago Midway Airport?

    Frontier Airlines is a budget airline that charges for most services, including checked baggage. The luggage allowance varies depending on the type of fare purchased by the passenger. Passengers who pick Basic Economy fare on Frontier flights from Denver to Chicago Midway Airport are only entitled to one small personal item. Passengers who pick Standard Economy fare can bring one personal item and one carry-on bag. The carry-on bag's maximum dimensions must be 24 × 16 × 10 inches, and it should fit in the overhead bin.

  • How do I get from Chicago Midway Airport (MDW) to the city center?

    You can take the CTA Orange Line train from Midway Airport to Downtown Chicago. The train runs every few minutes and takes about 25–30 minutes to reach the city center. Additionally, several airport shuttle companies operate at Midway Airport, offering shared or private shuttle services to the city center. The fares vary depending on the company and the type of service.

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

    In the last 3 days, the lowest price for a flight from Denver to Chicago Midway Airport was $90 for a one-way ticket and $178 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    Denver airport is called Denver Intl and the only airport in Chicago Midway Airport is Chicago Midway.

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Denver to Chicago are Southwest and Frontier. With an average price for the route of $271 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $194 and an overall rating of 5.7.

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

    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 Denver to Chicago Midway Airport.

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

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

    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 Chicago Midway Airport with an airline and back to Denver with another airline. Booking your flights between Denver and MDW 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 Denver to Chicago Midway Airport?

    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 Chicago Midway Airport from Denver 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 Denver to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $198 or less one-way and $276 or less round-trip.
  • Delta Air Lines offers flights from Denver to Chicago Midway Airport and has taken several steps to reduce carbon emissions and promote sustainability. The airline has committed to using 10% SAF by 2030. SAF is made from sustainable materials, such as waste oil, and it can reduce CO2 emissions by up to 80% compared to traditional jet fuel.
  • Chicago Midway Airport (MDW) serves various nearby cities including Bedford Park, Burbank, Bridgeview, Evergreen Park, Oak Lawn, Chicago Ridge, Alsip, Worth, Palos Hills, and Crestwood. These locations are all accessible by car from the airport.
  • Spirit Airlines provides wheelchair assistance on flights from Denver to Chicago Midway Airport from check-in to boarding and then upon arrival at the destination. Passengers can request a wheelchair at the airport or during the booking process. Airport staff will assist passengers with mobility issues in navigating through the airport terminals.
  • Denver International Airport (DEN) has three main passenger terminals. The Jeppesen Terminal is the Main Terminal, and it serves airlines such as Delta, and United Airlines, which offer flights from Denver to Chicago Midway Airport.
  • Frontier Airlines welcomes pets on board their flights from Denver to Chicago Midway Airport. They accept small cats and dogs as carry-on baggage in the aircraft cabin, and larger pets as checked baggage in the cargo hold. There is a fee for bringing a pet as a carry-on.

Prefer to fly direct from Denver to Chicago Midway Airport?

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

Direct departures

Denver Intl to Chicago Midway

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

Chicago Midway to Denver Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

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Sunday

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Southwest

See more direct flights

Reviews of the top airlines flying from Denver to Midway

 
See real verified KAYAK customer reviews for airlines flying from Denver to Chicago. 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 Denver to Midway? 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 4325 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

WiFi was not working and didn’t have a beverage service

8.0 ExcellentNick, Mar 2026
BOS - MDW
Read more Southwest reviews

WiFi was not working and didn’t have a beverage service

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

The seats were comfortable, and the boarding process was pretty smooth.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

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

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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 !!!!!!!

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Not clean and was told I would get a great seat and it was not great at all

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

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

Other airlines flying to Denver

Flight deals from the most popular airlines with KAYAK users flying the route