DEN - MDW

$107 Find Cheap Flights from Denver to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$199
Typical prices: $226-$396
Southwest
Sat 12/1Wed 12/5
DEN - MDW • Non-stop
Cheapest one-way
$107
Typical prices: $140-$260
Southwest
Mon 12/31
DEN - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 20m
Direct flights
+1
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $168 (round-trip)
Shortest trip • 4h 31m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
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

Tue, Dec 1 - Sat, Dec 5
Southwest Logo
6:05 pm - 9:30 pmDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
6:05 am - 7:55 amMDW  Chicago Midway-DEN Denver Intl
2h 50mnonstop
$199Southwest
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
4:15 pm - 7:35 pmDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:05 am - 8:00 amMDW  Chicago Midway-DEN Denver Intl
2h 55mnonstop
$199Southwest
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
6:05 pm - 9:30 pmDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
6:25 pm - 8:15 pmMDW  Chicago Midway-DEN Denver Intl
2h 50mnonstop
$199Southwest
Tue, Dec 1 - Wed, Dec 2
Southwest Logo
7:05 am - 10:30 amDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
6:05 am - 8:00 amMDW  Chicago Midway-DEN Denver Intl
2h 55mnonstop
$199Southwest
Wed, Dec 2 - Sat, Dec 5
Frontier Logo
11:59 pm - 2:41 pmDEN  Denver Intl-MDW Chicago Midway
13h 42m1 stop Orlando
Frontier Logo
10:20 am - 9:55 pmMDW  Chicago Midway-DEN Denver Intl
12h 35m1 stop Dallas/Fort Worth
$202Frontier
Mon, Nov 9 - Tue, Nov 10
Frontier Logo
10:41 am - 11:47 pmDEN  Denver Intl-MDW Chicago Midway
12h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:27 pm - 9:34 pmMDW  Chicago Midway-DEN Denver Intl
10h 07m1 stop Dallas/Fort Worth
$202Frontier
Mon, Dec 7 - Wed, Dec 9
Frontier Logo
6:41 am - 8:42 pmDEN  Denver Intl-MDW Chicago Midway
13h 01m1 stop Orlando
Frontier Logo
10:20 am - 9:55 pmMDW  Chicago Midway-DEN Denver Intl
12h 35m1 stop Dallas/Fort Worth
$202Frontier
Tue, Nov 17 - Wed, Nov 18
Delta Logo
11:08 am - 4:39 pmDEN  Denver Intl-MDW Chicago Midway
4h 31m1 stop Minneapolis St Paul
Delta Logo
10:34 am - 4:02 pmMDW  Chicago Midway-DEN Denver Intl
6h 28m1 stop Minneapolis St Paul
$219Delta
Sat, Dec 5 - Mon, Dec 7
Delta Logo
11:18 am - 4:50 pmDEN  Denver Intl-MDW Chicago Midway
4h 32m1 stop Minneapolis St Paul
Delta Logo
9:37 am - 3:15 pmMDW  Chicago Midway-DEN Denver Intl
6h 38m1 stop Detroit Metropolitan Wayne County
$259Delta
Sat, Dec 5 - Mon, Dec 7
Delta Logo
11:18 am - 4:50 pmDEN  Denver Intl-MDW Chicago Midway
4h 32m1 stop Minneapolis St Paul
Delta Logo
9:37 am - 3:15 pmMDW  Chicago Midway-DEN Denver Intl
6h 38m1 stop Detroit Metropolitan Wayne County
$260Delta
Booking Insights

Price, demand and travel trends for Denver to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Denver to Chicago Midway Airport typically range from $226 to $396. The lowest price found in the past 5 days was $199, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Denver to Chicago Midway Airport. It’s 9% cheaper than the average day, while Sunday is the most expensive, with prices 18% higher.

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

•January is the cheapest month to fly from Denver to Chicago Midway Airport at $216 round-trip.
•July ($391) and June ($384) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 81% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Denver to Chicago Midway Airport the cheapest?

Flights from Denver to Chicago Midway Airport are cheapest 7 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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.

Key details for Denver to Chicago Midway Airport flights

Low season

February

Cheapest flight

$107
Beat the crowds with an average 37% drop in travelers.
The most popular month to fly with an average 24% increase in travelers.
One-way 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

Your Denver to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Denver to Chicago Midway Airport?

    These are the earliest and latest flight times available from Denver to Chicago Midway Airport:

    • Earliest: departs at 5:05 am and lands at 7:25 am
    • Latest: departs at 10:35 pm and lands at 12:55 am.

    The flight takes about 2h 20m.

  • What cabin classes can I book on flights from Denver to Chicago Midway Airport?

    Only Economy Class is available on flights from Denver to Chicago Midway Airport.

  • How long is a flight from Denver to Chicago Midway Airport?

    A nonstop flight from Denver to Chicago Midway Airport takes 2h 20m, covering 893 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Denver to Chicago Midway Airport flight?

    Round-trip flights from Denver to Chicago Midway Airport range from $226 to $396, with an average of $298 over the past 12 months. Anything below $226 counts as a good deal.

  • How expensive are last-minute Denver to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 34% above the $298 route average. Book 7 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Denver to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $168 round-trip via Dallas/Fort Worth (DFW), compared to $305 for nonstop.

  • What is the standard checked-bag allowance on flights from Denver to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Denver to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Airbus A321neo variants.

  • How are flight departures from Denver to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Denver to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

  • Have flight prices from Denver to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $199 to $1,736. That means the highest observed fare was about 9x higher than the lowest one.

  • Which airlines offer Wi-Fi on Denver to Chicago Midway Airport flights?

    JetBlue is the only airline on the Denver to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Denver to Chicago Midway Airport looking right now?

    One-way fares from Denver to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $113, which is 44% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Denver to Chicago Midway Airport?

    Flights from Denver to Chicago Midway Airport usually depart from Denver Intl (DEN) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Denver to Chicago Midway Airport pass through?

    One-stop flights from Denver to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 46% of one-stop connections
    • Minneapolis St Paul (MSP) - 23% of one-stop connections
    • Dallas/Fort Worth (DFW) - 15% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 8% of one-stop connections

  • Can I save money by using flexible dates for flights from Denver to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 23% on flights from Denver to Chicago Midway Airport. Wednesday is the cheapest departure day at $272 round-trip on average, while Sunday is the most expensive at $352, a difference of $80.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Denver to Chicago Midway Airport?

    Only Southwest operates flights between Denver and Chicago Midway Airport.

  • How much time can I save by choosing a different layover airport from Denver to Chicago Midway Airport?

    Flying via Wichita Eisenhower National (ICT) gives the shortest average 1-stop total travel time at 4h 31m, compared with 6h 03m via Detroit Metropolitan Wayne County (DTW) and 6h 10m via Minneapolis St Paul (MSP).

  • What is the time difference between Denver and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour ahead of Denver (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Denver to Chicago Midway Airport flights?

    Among airlines operating Denver to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Denver to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • 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.

Your guide to booking Denver to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $272, about $80 less than Sunday fares (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Denver to Chicago Midway Airport trip for January. Fares historically average $216 round-trip in that month - typically $175 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Dallas/Fort Worth Airport (DFW) can be cheaper than flying direct. The cheapest layover option averages $168 round-trip on this route - about $136 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel
  • 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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Denver Intl

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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More options for your flight from Denver to Midway

Complete your trip to Chicago with a hotel stay or car rental