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Midway

$104+ Cheap flights from Denver (DEN) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Sep 8 — Sep 151
Tue 9/8
Tue 9/15
1 adult, Economy
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Find cheap flights from Denver to Midway with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Denver Intl to Chicago Midway are usually found in November or December, booked 54 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Denver to Midway

Cheapest flights from Denver to Midway
Explore the most affordable flight options available from Denver to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 2026.

This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:09 am -
1 stop9h 22m
Mon 8/316:05 am -
1 stop8h 56m
Deal found 8/5$171
This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:48 pm -
1 stop10h 10m
Tue 10/131:02 pm -
1 stop8h 02m
Deal found 8/5$172
This FlightHub deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:43 am -
1 stop11h 04m
Sat 8/2911:45 am -
1 stop11h 20m
Deal found 8/7$173
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:43 am -
1 stop11h 04m
Tue 9/811:50 am -
1 stop11h 15m
Deal found 8/7$175
This Travelocity deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:48 pm -
1 stop10h 10m
Wed 10/216:40 am -
1 stop8h 20m
Deal found 8/4$177
This Priceline deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:43 am -
1 stop11h 04m
Wed 9/211:50 am -
1 stop11h 20m
Deal found 8/6$178
This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:44 am -
1 stop12h 00m
Mon 9/1412:54 pm -
1 stop9h 55m
Deal found 8/5$182
This FlightHub deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:59 pm -
1 stop9h 56m
Fri 8/289:26 pm -
1 stop10h 02m
Deal found 8/5$183
This Expedia deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:30 am -
1 stop10h 28m
Sun 10/2512:03 pm -
1 stop11h 30m
Deal found 8/4$187

Find flight deals from Denver to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Denver (DEN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$171
(Trip.com)

One-way from

$104
(Frontier)

Popular in

June

Cheapest in

November

Average price

$307

Good round-trip deal

$309 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Denver Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Denver Intl-Chicago Midway flights.
Search Deals
From Denver Intl to Chicago Midway
Search Deals
One-way flight from Denver Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Denver Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Denver Intl to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Denver to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Denver to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Sat 10/10

5:35 pm-8:55 pm

Nonstop2h 20m

Chicago Midway

Tue 10/13

7:40 am-9:15 am

Nonstop2h 35m

$237

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Mon 9/14

8:25 pm-11:50 pm

Nonstop2h 25m

Chicago Midway

Mon 9/21

3:15 pm-7:20 pm

1 stop5h 05m

$257

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Wed 9/23

11:15 am-4:05 pm

1 stop3h 50m

Chicago Midway

Wed 9/30

8:20 am-12:20 pm

1 stop5h 00m

$266

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Fri 9/25

6:30 pm-10:05 pm

Nonstop2h 35m

Chicago Midway

Sun 9/27

7:55 am-9:40 am

Nonstop2h 45m

$266

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Thu 9/17

11:00 am-5:00 pm

1 stop5h 00m

Chicago Midway

Mon 9/21

3:15 pm-7:20 pm

1 stop5h 05m

$267

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Thu 9/3

11:00 am-5:00 pm

1 stop5h 00m

Chicago Midway

Tue 9/8

8:50 pm-10:30 pm

Nonstop2h 40m

$276

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Fri 10/9

8:55 pm-12:15 am

Nonstop2h 20m

Chicago Midway

Mon 10/12

9:20 pm-11:00 pm

Nonstop2h 40m

$296

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Wed 9/23

10:55 am-6:33 pm

1 stop6h 38m

Chicago Midway

Sat 9/26

1:19 pm-5:21 pm

1 stop5h 02m

$298

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Thu 9/3

8:25 pm-11:50 pm

Nonstop2h 25m

Chicago Midway

Sat 9/5

6:00 pm-7:45 pm

Nonstop2h 45m

$306
Cheapest one-way

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Sat 9/5

5:20 pm-8:50 pm

Nonstop2h 30m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/8

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Denver to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Denver to Midway in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Denver-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Denver-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Denver-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Denver-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Denver-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Denver to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Denver with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Denver to Chicago Midway Airport

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

To ensure you get the cheapest price possible for a flight from Denver to Chicago Midway Airport, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Denver to Chicago Midway Airport?

Currently, November is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $218). Flying from Denver to Chicago Midway Airport in June is currently the most expensive (average of $434). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DEN to MDW?

Find hourly flight availability from Denver to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 9, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 30% on flights from Denver to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Denver to Midway. Price data was last updated on August 8, 2026.

Travelers seeking maximum savings on their Denver to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Denver to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Denver to Chicago Midway Airport flights typically cost between $227 and $413 in August.
The cheapest round-trip price found within the last 5 days was $171 on Frontier (Aug 27-Aug 31).

The best insider tips for Denver to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Denver to Chicago Midway Airport trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Emily Zemler

Emily Zemler

Expert on DEN

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 9, 2026.
See what other customers who have flown with Southwest and Frontier from Denver to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,214 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,715 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Denver to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Denver to Chicago Midway?

    If you book a flight to Chicago Midway from Denver, you will be flying from Denver Intl, which is the city’s only airport. Denver Intl (DEN) is located 18.5 mi from the center of Denver. There are 3 flights from Denver Intl to Chicago Midway per day from 2 different airlines.

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

    Airlines like Southwest fly from Denver to Chicago Midway Airport in about 2h 20m. The time it takes to get you to your destination is usually consistent. There are 893 mi between Denver and Chicago Midway Airport. Generally, flights for this route are nonstop.

  • What are the cheapest airlines flying from Denver to Chicago Midway Airport round-trip?

    Currently priced at $84, Frontier will fly you from Denver to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $196. Users have found that Frontier is 72% cheaper than the other options available to this destination.

  • What are the cheapest flights from Denver to Chicago Midway Airport?

    On average you can expect to pay $332 for a flight from Denver to Chicago Midway Airport. The cheapest flight overall is $102 while the most popular route, (Denver Intl - Chicago Midway) is currently priced at $158.

  • Can I find deals for flights from Denver to Midway that include hotel bookings?

    Yes. In addition to deals on Denver to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Denver to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Denver to Midway.

  • Can I find deals for business class flights from Denver to Midway?

    Yes. Cheapflights offers flight deals from Denver to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, November is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $218). Flying from Denver to Chicago Midway Airport in June is currently the most expensive (average of $434). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Denver to Midway

Discover the top 2 airlines that operate flights from Denver to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$194FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$197Average$357FlexibilityNo cancel feeOn-time63%

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