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$76+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Denver Intl to Chicago Midway are usually found in September or June, booked 89 days in advance, depart on a Saturday or Tuesday and return on a Saturday

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 mayo 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$149
(Cheapflightsfares)

One-way from

$76
(Southwest)

Popular in

December

Cheapest in

September

Average price

$178

Good round-trip deal

$188 or less

Good one-way deal

$103 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. 18% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in May 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 mayo 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/153:42 pmDEN - MDW
Nonstop2h 26mFrontier
mar. 5/272:44 pmMDW - DEN
Nonstop2h 49mFrontier
Deal found 4/29$149
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/47:25 pmDEN - MDW
Nonstop2h 25mSouthwest
mié. 6/115:15 amMDW - DEN
Nonstop2h 35mSouthwest
Deal found 4/29$151
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/1212:55 amDEN - MDW
1 stop6h 46mDelta
jue. 6/196:47 pmMDW - DEN
1 stop6h 34mDelta
Deal found 4/29$217

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 mayo 1, 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

jue. 5/15

3:42 pm-7:08 pm

Nonstop2h 26m

Chicago Midway

mar. 5/27

2:44 pm-4:33 pm

Nonstop2h 49m

$149

DenverChicago

DEN - MDW

DENMDW

Denver Intl

mié. 6/4

5:55 am-9:20 am

Nonstop2h 25m

Chicago Midway

mié. 6/4

4:35 pm-6:20 pm

Nonstop2h 45m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

jue. 6/12

12:55 am-8:41 am

1 stop6h 46m

Chicago Midway

vie. 6/20

6:47 pm-12:21 am

1 stop6h 34m

$217

DenverChicago

DEN - MDW

DENMDW

Denver Intl

sáb. 7/5

5:00 am-8:25 am

Nonstop2h 25m

$76

DenverChicago

DEN - MDW

DENMDW

Denver Intl

jue. 5/15

3:42 pm-7:08 pm

Nonstop2h 26m

$96

DenverChicago

DEN - MDW

DENMDW

Denver Intl

jue. 6/12

12:55 am-8:41 am

1 stop6h 46m

$109

DenverChicago

DEN - MDW

DENMDW

Denver Intl

dom. 6/1

5:50 pm-6:10 pm

1 stop23h 20m

$140

DenverChicago

DEN - MDW

DENMDW

Denver Intl

dom. 6/1

9:26 am-7:14 pm

2 stops32h 48m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*2 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Denver-Chicago Midway Airport flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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
Airports
DEN

Consider using the A Line train for a quick 37-minute ride from Union Station to DEN, avoiding costly taxis.

Read more about DENby Emily Zemler
MDW

Use the Orange Line for a quick, 30-minute ride from MDW to downtown Chicago, operating nearly 24 hours.

Read more about MDWby Ramsey Qubein
Our travel experts
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 April 25, 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 89 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 mayo 1, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 24% 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 March 30, 2025.

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 mayo 1, 2025.
To help decide which airline to fly from Denver to Chicago, see what other customers have to say about Southwest, Delta and Frontier. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 5 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 $149, 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 Delta - these airlines can fly you to your destination from $151 and $217, respectively. Users have found that Frontier is 19% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Denver to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $76 on Southwest. Other airlines that offer cheap prices include Frontier from $97 and Delta from $109 one-way.

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

    On average you can expect to pay $210 for a flight from Denver to Chicago Midway Airport. The cheapest flight overall is $75 while the most popular route, (Denver Intl - Chicago Midway) is currently priced at $104.

  • 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 Denver?

Book flights to Denver if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$144FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$163Average$255FlexibilityNo cancel feeOn-time63%

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