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Midway

$69+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 Wednesday

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 August 14, 2025.

Round-trip from

$121
(Frontier)

One-way from

$69
(Southwest)

Popular in

December

Cheapest in

February

Average price

$251

Good round-trip deal

$167 or less

Good one-way deal

$122 or less
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 August 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 August 14, 2025.

This Frontier deal was found by Cheapflights users on 8/14. 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 9/156:10 amDEN - MDW
1 stop6h 01mFrontier
Fri 9/264:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/14$121
This Frontier deal was found by Cheapflights users on 8/14. 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.
Thu 9/41:12 pmDEN - MDW
1 stop9h 08mFrontier
Mon 9/84:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/14$123
This Mytrip deal was found by Cheapflights users on 8/13. 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.
Wed 9/35:00 pmDEN - MDW
1 stop18h 46mFrontier
Mon 9/84:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/13$124
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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.
Fri 9/1212:28 pmDEN - MDW
Nonstop2h 25mFrontier
Mon 9/154:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/14$125
This CheapOair deal was found by Cheapflights users on 8/12. 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 10/317:10 pmDEN - MDW
Nonstop2h 28mFrontier
Mon 11/34:29 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 8/12$126
This Frontier deal was found by Cheapflights users on 8/14. 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.
Fri 9/512:28 pmDEN - MDW
Nonstop2h 25mFrontier
Mon 9/84:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/14$127
This FlightHub deal was found by Cheapflights users on 8/14. 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.
Fri 9/1212:28 pmDEN - MDW
Nonstop2h 25mFrontier
Tue 9/162:32 pmMDW - DEN
1 stop19h 34mFrontier
Deal found 8/14$130
This CheapOair deal was found by Cheapflights users on 8/14. 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
Sun 11/911:21 amMDW - DEN
1 stop13h 56mFrontier
Deal found 8/14$131
This CheapOair deal was found by Cheapflights users on 8/14. 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 11/612:59 amDEN - MDW
1 stop16h 40mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 8/14$133
This CheapOair deal was found by Cheapflights users on 8/14. 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 9/118:15 pmDEN - MDW
1 stop23h 31mFrontier
Mon 9/154:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/14$134
This Frontier deal was found by Cheapflights users on 8/12. 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 9/1512:28 pmDEN - MDW
Nonstop2h 25mFrontier
Mon 9/224:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/12$135

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 14, 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

Mon 10/6

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Sat 10/11

5:20 pm-11:43 pm

1 stop7h 23m

$121

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

10:01 am-11:20 pm

1 stop12h 19m

Chicago Midway

Mon 10/20

6:24 pm-8:08 pm

Nonstop2h 44m

$121

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 9/2

12:54 am-2:01 pm

1 stop12h 07m

Chicago Midway

Mon 9/8

4:48 pm-6:26 pm

Nonstop2h 38m

$123

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 10/24

8:58 pm-12:24 am

Nonstop2h 26m

Chicago Midway

Mon 10/27

6:24 pm-8:08 pm

Nonstop2h 44m

$125

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 11/7

7:10 pm-10:38 pm

Nonstop2h 28m

Chicago Midway

Mon 11/10

4:29 pm-6:17 pm

Nonstop2h 48m

$127

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/5

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Mon 9/8

4:48 pm-6:26 pm

Nonstop2h 38m

$127

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 10/16

9:12 pm-12:36 am

Nonstop2h 24m

Chicago Midway

Mon 10/20

5:20 pm-10:59 pm

1 stop6h 39m

$128

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/12

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Sun 9/14

6:30 am-10:53 pm

1 stop17h 23m

$130

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 10/24

7:15 am-3:12 pm

1 stop6h 57m

Chicago Midway

Sun 10/26

6:24 pm-8:08 pm

Nonstop2h 44m

$130

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/12

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Tue 9/16

2:32 pm-9:06 am

1 stop19h 34m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 16 results
1
2

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 drinks, enhancing the short flight experience.


Enjoy free messaging and in-flight entertainment on your device with Southwest's Wi-Fi service.

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 August 8, 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 August 14, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 46% 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 10, 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.

Weekly flight availability from Denver to Chicago Midway Airport

Explore weekly flight availability from Denver to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2025.

The most flights from DEN to MDW are scheduled on a Thursday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 14, 2025.
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
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,219 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 6 flights from Denver Intl to Chicago Midway per day from 2 different airlines.

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

    Currently priced at $63, 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 $159. Users have found that Frontier is 70% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Denver to Chicago Midway Airport?

    The top 3 most reliable airlines when flying from Denver to Chicago Midway Airport are Southwest (56%), Frontier (48%) and United Airlines (0%).

  • 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 $76 while the most popular route, (Denver Intl - Chicago Midway) is currently priced at $97.

  • 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

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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$164FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$249FlexibilityNo cancel feeOn-time63%

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