DEN - MDW

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

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$158
Typical prices: $217-$423
Frontier
Sat 10/24Mon 10/26
DEN - MDW • 1 stop
Cheapest non-stop
$196
Typical prices: $201-$362
JetBlue
Tue 9/22Sat 9/26
DEN - MDW • Non-stop
Advice from real travelers
Southwest includes a carry-on and personal item; checked bags now cost extra.
Frontier Economy Bundle adds seat choice; Premium Bundle adds legroom for $20.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 22m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $228 (round-trip)
Shortest trip • 6h 09m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 42% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Denver to Midway

Sat, Oct 24 - Mon, Oct 26
Frontier Logo
6:05 am - 12:17 pmDEN  Denver Intl-MDW Chicago Midway
5h 12m1 stop Dallas/Fort Worth
Frontier Logo
1:12 pm - 9:49 pmMDW  Chicago Midway-DEN Denver Intl
9h 37m1 stop Dallas/Fort Worth
$158Frontier
Tue, Oct 27 - Thu, Oct 29
Frontier Logo
10:56 am - 9:53 pmDEN  Denver Intl-MDW Chicago Midway
9h 57m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:03 pm - 10:33 pmMDW  Chicago Midway-DEN Denver Intl
11h 30m1 stop Atlanta Hartsfield-Jackson
$158Frontier
Fri, Oct 2 - Mon, Oct 5
Frontier Logo
10:44 am - 5:51 pmDEN  Denver Intl-MDW Chicago Midway
6h 07m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:54 pm - 9:49 pmMDW  Chicago Midway-DEN Denver Intl
9h 55m1 stop Dallas/Fort Worth
$158Frontier
Thu, Oct 1 - Sat, Oct 3
Frontier Logo
10:44 am - 11:44 pmDEN  Denver Intl-MDW Chicago Midway
12h 00m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:06 pm - 9:49 pmMDW  Chicago Midway-DEN Denver Intl
9h 43m1 stop Dallas/Fort Worth
$158Frontier
Tue, Sep 22 - Sat, Sep 26
JetBlue Logo
6:30 am - 9:50 amDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
JetBlue Logo
5:05 pm - 6:50 pmMDW  Chicago Midway-DEN Denver Intl
2h 45mnonstop
$196JetBlue
Tue, Sep 22 - Sat, Sep 26
JetBlue Logo
9:35 am - 7:10 pmDEN  Denver Intl-MDW Chicago Midway
8h 35m1 stop Austin Bergstrom
JetBlue Logo
5:05 pm - 6:50 pmMDW  Chicago Midway-DEN Denver Intl
2h 45mnonstop
$206JetBlue
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
8:35 am - 11:55 amDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:15 am - 7:55 amMDW  Chicago Midway-DEN Denver Intl
2h 40mnonstop
$213Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
7:25 pm - 10:55 pmDEN  Denver Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
7:20 pm - 8:55 pmMDW  Chicago Midway-DEN Denver Intl
2h 35mnonstop
$213Southwest
Wed, Sep 16 - Sat, Sep 19
Southwest Logo
6:30 am - 9:50 amDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:00 pm - 7:45 pmMDW  Chicago Midway-DEN Denver Intl
2h 45mnonstop
$213Southwest
Sat, Sep 19 - Tue, Sep 22
Delta Logo
6:30 am - 12:39 pmDEN  Denver Intl-MDW Chicago Midway
5h 09m1 stop Detroit Metropolitan Wayne County
Delta Logo
2:00 pm - 8:05 pmMDW  Chicago Midway-DEN Denver Intl
7h 05m1 stop Minneapolis St Paul
$233Delta
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.

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

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from Denver usually cost between $227 and $413 in October.
The lowest price found in the past 5 days was $158 on Frontier (Oct 21-Oct 24).

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

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 Friday, and avoid Sundays for better deals.

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

The cheapest month for flights from Denver to Chicago Midway Airport is November, where tickets cost $218 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $434 and $393 respectively.

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

No, with an average price for the route of $341, prices are generally cheapest when you fly direct.

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

To get a below average price on the flight from Denver to Chicago Midway Airport, you should book around 5 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Expert advice

Expert advice for your flight from Denver to Midway

 
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 season

January

Cheapest flight

$103
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 40% increase in price.
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

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 5 days, the lowest price for a flight from Denver to Chicago Midway Airport was $103 for a one-way ticket and $158 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, Delta, and Alaska Airlines 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 $360 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 5.6.

  • 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 $203 or less one-way and $312 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

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

Southwest

Sunday

Southwest

Southwest

See more direct flights

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

Other airlines flying to Denver