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Midway

$63+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheapflights Tip: The best prices from Denver Intl to Chicago Midway are usually found in February or September, booked 75 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$119
(Cheapflightsfares)

One-way from

$63
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$165

Good round-trip deal

$170 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Denver Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Denver Intl-Chicago Midway flights.
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From Denver Intl to Chicago Midway
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One-way flight from Denver Intl to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Denver Intl to Chicago Midway.
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Price to beat on a one-way flight from Denver Intl to Chicago Midway.
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Find 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 September 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:15 pmDEN - MDW
Nonstop2h 21mFrontier
Mon 12/82:45 pmMDW - DEN
Nonstop2h 45mFrontier
Deal found 9/27$119
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/178:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 12/52:45 pmMDW - DEN
Nonstop2h 45mFrontier
Deal found 9/29$120
This Mytrip deal was found by Cheapflights users on 9/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2512:25 pmDEN - MDW
1 stop9h 22mFrontier
Mon 10/2712:11 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/27$121
This CheapOair deal was found by Cheapflights users on 9/27. 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.
Thu 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/96:30 amMDW - DEN
1 stop26h 06mFrontier
Deal found 9/27$122
This Trip.com deal was found by Cheapflights users on 9/27. 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.
Sun 10/2612:34 amDEN - MDW
1 stop9h 43mFrontier
Thu 11/612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/27$124
This CheapOair deal was found by Cheapflights users on 9/26. 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.
Sun 10/2612:34 amDEN - MDW
1 stop9h 43mFrontier
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/26$125
This CheapOair deal was found by Cheapflights users on 9/27. 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.
Fri 10/247:49 amDEN - MDW
Nonstop2h 27mFrontier
Sun 10/2610:30 amMDW - DEN
1 stop22h 06mFrontier
Deal found 9/27$126
This Priceline deal was found by Cheapflights users on 9/28. 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.
Sat 10/1812:25 pmDEN - MDW
1 stop9h 22mFrontier
Thu 10/236:24 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 9/28$128
This CheapOair deal was found by Cheapflights users on 9/27. 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.
Fri 11/78:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/27$129
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/199:12 pmDEN - MDW
Nonstop2h 24mFrontier
Mon 10/2010:56 pmMDW - DEN
1 stop11h 36mFrontier
Deal found 9/29$130
This CheapOair deal was found by Cheapflights users on 9/27. 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.
Fri 10/178:58 pmDEN - MDW
Nonstop2h 26mFrontier
Mon 10/209:00 amMDW - DEN
1 stop23h 36mFrontier
Deal found 9/27$132
This Priceline deal was found by Cheapflights users on 9/28. 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.
Mon 10/612:28 pmDEN - MDW
Nonstop2h 25mFrontier
Thu 10/3012:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/28$134

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 September 29, 2025.
Use the filters below to find and compare flights from Denver to Chicago Midway Airport that are best for you.

Fly from

Denver

Fly to

Midway

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 10/21

7:55 am-2:40 pm

1 stop5h 45m

Chicago Midway

Tue 10/21

5:30 pm-8:50 pm

1 stop4h 20m

$162

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/25

5:25 pm-8:45 pm

Nonstop2h 20m

Chicago Midway

Mon 10/27

9:20 am-11:00 am

Nonstop2h 40m

$172

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 11/22

8:25 pm-11:45 pm

Nonstop2h 20m

Chicago Midway

Thu 11/27

5:30 am-7:10 am

Nonstop2h 40m

$181

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 11/6

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Mon 11/10

9:40 pm-11:15 pm

Nonstop2h 35m

$181

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 11/20

5:00 am-11:25 am

1 stop5h 25m

Chicago Midway

Mon 11/24

9:40 pm-11:15 pm

Nonstop2h 35m

$191

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sun 12/7

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Mon 12/8

6:00 pm-7:40 pm

Nonstop2h 40m

$197

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 12/19

5:20 am-8:45 am

Nonstop2h 25m

Chicago Midway

Mon 1/19

9:55 am-2:30 pm

1 stop5h 35m

$205

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 11/8

5:45 am-11:45 am

1 stop5h 00m

Chicago Midway

Sun 11/9

7:45 am-9:25 am

Nonstop2h 40m

$207

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 11/26

8:20 pm-11:40 pm

Nonstop2h 20m

Chicago Midway

Sat 12/6

5:15 pm-6:55 pm

Nonstop2h 40m

$211

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 10/22

8:05 am-1:10 pm

1 stop4h 05m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 18 results
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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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.

The best insider tips for Denver to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Denver to Chicago Midway Airport trip
Airlines
Southwest

Southwest offers free snacks and non-alcoholic beverages, enhancing the in-flight experience.


Southwest’s Rapid Rewards program offers points for flights, with no blackout dates for redemption.

Read more about Southwestby Marisa Garcia
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.


Frontier offers complimentary water onboard; request it from the flight attendants.

Read more about Frontierby Marisa Garcia
Airports
DEN

For a quick security experience, reserve a time online for general screening at DEN. It's a convenient option for domestic travelers.

Read more about DENby Emily Zemler
MDW

Take the Orange Line from MDW to reach downtown Chicago in under 30 minutes. It's a cost-effective and efficient option.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest and Frontier

Marisa Garcia

Marisa Garcia

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

Ramsey Qubein

Ramsey Qubein

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 Zemler

Emily Zemler

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

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?

Use this chart to determine the optimal time to book a round-trip flight from Denver to Midway. Price data was last updated on September 26, 2025.

To ensure you get the cheapest price possible for a flight from Denver to Chicago Midway Airport, you should look to book at least 75 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, April is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $160). Flying from Denver to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 29, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 44% 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 September 28, 2025.

Travelers seeking maximum savings on their Denver to Chicago Midway Airport flight should consider departing on Tuesday 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.

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 September 29, 2025.
See what other customers who have flown with Southwest, American Airlines, 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
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,157 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 3 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 5h 45m. The time it takes to get you to your destination can typically vary by up to . There are 893 mi between Denver and Chicago Midway Airport.

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

    Currently priced at $67, 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. Search Cheapflights for deals from Southwest and American Airlines - these airlines can fly you to your destination from $158 and $195, respectively. Users have found that Frontier is 68% 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 $217 for a flight from Denver to Chicago Midway Airport. The cheapest flight overall is $78 while the most popular route, (Denver Intl - Chicago Midway) is currently priced at $86.

  • 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, April is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $160). Flying from Denver to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 3 airlines flying from Denver to Midway

Discover the top 3 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$169FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$254FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$195Average$247FlexibilityNo cancel feeOn-time71%

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