DEN - MDW

$52 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 5/29. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flights from Denver to Midway

 
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.

Recent round-trip flight deals from Denver to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Denver to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
5:26 pm - 8:53 pmDEN-MDW
2h 27mnonstop
Frontier Logo
2:44 pm - 4:33 pmMDW-DEN
2h 49mnonstop
$104Frontier
Find Deal
Thu, Jul 3 - Sat, Jul 5
Frontier Logo
5:26 pm - 8:53 pmDEN-MDW
2h 27mnonstop
Frontier Logo
2:44 pm - 4:36 pmMDW-DEN
2h 52mnonstop
$106Frontier
Find Deal
Thu, Jun 5 - Sat, Jun 7
Frontier Logo
8:15 am - 11:41 amDEN-MDW
2h 26mnonstop
Frontier Logo
12:35 pm - 2:19 pmMDW-DEN
2h 44mnonstop
$109Frontier
Find Deal
Fri, Jul 18 - Mon, Jul 21
Southwest Logo
9:30 pm - 12:55 amDEN-MDW
2h 25mnonstop
Southwest Logo
5:15 am - 6:50 amMDW-DEN
2h 35mnonstop
$151Southwest
Find Deal
Wed, Jun 11 - Wed, Jul 16
Frontier Logo
8:15 am - 11:40 amDEN-MDW
2h 25mnonstop
Frontier Logo
12:35 pm - 2:23 pmMDW-DEN
2h 48mnonstop
$152Frontier
Find Deal
Fri, Jun 20 - Mon, Jun 23
Southwest Logo
3:30 pm - 6:50 pmDEN-MDW
2h 20mnonstop
Southwest Logo
6:35 am - 8:10 amMDW-DEN
2h 35mnonstop
$160Southwest
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
7:15 am - 1:40 pmDEN-MDW
5h 25m1 stop
Southwest Logo
9:35 am - 11:15 amMDW-DEN
2h 40mnonstop
$161Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
12:55 am - 8:41 amDEN-MDW
6h 46m1 stop
Delta Logo
7:21 pm - 11:22 pmMDW-DEN
5h 01m1 stop
$217Delta
Find Deal
Thu, Jun 12 - Fri, Jun 20
Delta Logo
12:55 am - 8:45 amDEN-MDW
6h 50m1 stop
Delta Logo
9:30 am - 2:03 pmMDW-DEN
5h 33m1 stop
$221Delta
Find Deal
Wed, Oct 8 - Tue, Oct 14
Delta Logo
12:55 am - 8:40 amDEN-MDW
6h 45m1 stop
Delta Logo
6:00 am - 12:42 pmMDW-DEN
7h 42m1 stop
$249Delta
Find Deal
Mon, May 12 - Wed, May 14
Expert advice

Expert advice for your flight from Denver to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on and seat choice, ideal for budget-conscious travelers.


Frontier's Premium Bundle offers extra legroom and priority boarding for just $20 more than Economy.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers two free checked bags, saving money for travelers with luggage.


Southwest's EarlyBird Check-In ensures a better boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Airports
DEN

Use the West Security Checkpoint for faster screening; it allows liquids and laptops to stay in bags.

Read more about DENby Harriet Baskas
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on DEN

Harriet Baskas

Harriet Baskas

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.

Read more
Useful Info

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 Saturday and more expensive on a Sunday. On your return trip to Denver, you should consider flying back on a Saturday, 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 $123 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $256 and $233 respectively.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

February

High season

May

Cheapest flight

$52
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 4% 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 $52 for a one-way ticket and $104 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, 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 $255 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 $144 and an overall rating of 5.9.

  • 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 $103 or less one-way and $188 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?

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

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Direct returns

Chicago Midway to Denver Intl

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

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 4295 reviews
8.2Boarding
8.6Crew
7.6Entertainment
7.1Food
8.0Comfort
Airline reviews

I would have liked to arrive on time - not 5 hours late!

4.0 OkayAnonymous, Apr 2025DEN - SEA
Read more Southwest reviews

I would have liked to arrive on time - not 5 hours late!

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

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.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

My original flight was extremely delayed but I was able to join the standby list for an earlier flight. I was grateful for this feature but I wish I could’ve gotten my standby confirmation sooner.

I like that it was on time and the staff was friendly.

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Since the flight wasn’t full, we had some extra room. Crew was great

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Everything went as planned. Crew was great. Seats were still not that comfortable.

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The seats were extremely hard and uncomfortable, even for a budget airline.

Boarding was very well executed. Got my bag right away.

Overall experience good. There was no food and seats were not terribly comfortable.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

There were a lot of issues every step of the process. Check in, security, boarding, and dealing with luggage. Plus the money you think you are saving you end up using in hidden fees.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.