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Cheap flights from Denver to Chicago from $84

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Denver to Chicago departing on 4/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Denver to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:20 pm - 12:37 am
DEN
-
MDW
8h 17m
1 stop
Frontier Logo
2:15 pm - 10:29 pm
MDW
-
DEN
9h 14m
1 stop
$152Frontier
Sat, Apr 11 - Tue, Apr 21
Frontier Logo
3:20 pm - 12:37 am
DEN
-
MDW
8h 17m
1 stop
Frontier Logo
5:11 pm - 11:58 pm
MDW
-
DEN
7h 47m
1 stop
$155Frontier
Sat, Apr 11 - Mon, Apr 13
Frontier Logo
1:09 pm - 10:19 pm
DEN
-
MDW
8h 10m
1 stop
Frontier Logo
6:00 am - 12:09 pm
MDW
-
DEN
7h 09m
1 stop
$159Frontier
Thu, Apr 16 - Thu, Apr 23
Frontier Logo
1:09 pm - 10:19 pm
DEN
-
MDW
8h 10m
1 stop
Frontier Logo
2:20 pm - 11:03 pm
MDW
-
DEN
9h 43m
1 stop
$160Frontier
Fri, May 8 - Sat, May 9
Frontier Logo
3:20 pm - 12:37 am
DEN
-
MDW
8h 17m
1 stop
Frontier Logo
6:00 am - 12:09 pm
MDW
-
DEN
7h 09m
1 stop
$161Frontier
Sat, Apr 11 - Mon, Apr 13
Frontier Logo
1:09 pm - 10:14 pm
DEN
-
MDW
8h 05m
1 stop
Frontier Logo
6:00 am - 12:14 pm
MDW
-
DEN
7h 14m
1 stop
$162Frontier
Wed, Apr 15 - Sat, Apr 18
Frontier Logo
8:00 am - 9:37 pm
DEN
-
MDW
12h 37m
1 stop
Frontier Logo
2:15 pm - 10:29 pm
MDW
-
DEN
9h 14m
1 stop
$164Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
11:59 pm - 9:58 am
DEN
-
MDW
8h 59m
1 stop
Frontier Logo
2:15 pm - 10:29 pm
MDW
-
DEN
9h 14m
1 stop
$165Frontier
Sat, Apr 25 - Tue, Apr 28
Frontier Logo
6:25 pm - 3:59 pm
DEN
-
MDW
20h 34m
1 stop
Frontier Logo
4:46 pm - 11:58 pm
MDW
-
DEN
8h 12m
1 stop
$166Frontier
Thu, Apr 9 - Sun, Apr 12
Frontier Logo
1:09 pm - 10:14 pm
DEN
-
MDW
8h 05m
1 stop
Frontier Logo
6:00 am - 10:19 pm
MDW
-
DEN
17h 19m
2 stops
$167Frontier
Wed, Apr 29 - Sat, May 2

Southwest flights from Denver to Chicago Midway Airport

Our best Southwest deals on Denver to Chicago Midway Airport flight tickets
Southwest
Apr 14
DEN6:35 amDenver Intl
2h 20m
MDW9:55 amChicago Midway
Apr 14
MDW8:50 pmChicago Midway
2h 45m
DEN10:35 pmDenver Intl
$177
Southwest
Apr 14
DEN11:05 amDenver Intl
4h 30m
1 stop
MDW4:35 pmChicago Midway
Apr 14
MDW8:50 pmChicago Midway
2h 45m
DEN10:35 pmDenver Intl
$183
Southwest
Apr 22
DEN5:55 pmDenver Intl
2h 35m
MDW9:30 pmChicago Midway
Apr 26
MDW6:00 amChicago Midway
2h 40m
DEN7:40 amDenver Intl
$187

Frontier flights from Denver to Chicago Midway Airport

Our best Frontier deals on Denver to Chicago Midway Airport flight tickets
Frontier
May 13
DEN1:09 pmDenver Intl
8h 10m
1 stop
MDW10:19 pmChicago Midway
May 18
MDW6:15 amChicago Midway
10h 34m
1 stop
DEN3:49 pmDenver Intl
$146
Frontier
Apr 27
DEN1:07 pmDenver Intl
8h 12m
1 stop
MDW10:19 pmChicago Midway
Apr 30
MDW8:25 amChicago Midway
9h 28m
1 stop
DEN4:53 pmDenver Intl
$151
Frontier
Apr 11
DEN3:20 pmDenver Intl
8h 17m
1 stop
MDW12:37 amChicago Midway
Apr 21
MDW2:15 pmChicago Midway
9h 14m
1 stop
DEN10:29 pmDenver Intl
$152

momondo Fare Finder

 
Customize your flight search to find flights from Denver to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated March 5, 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

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 4/11

3:20 pm-12:37 am

1 stop8h 17m

Chicago Midway

Tue 4/21

2:15 pm-10:29 pm

1 stop9h 14m

$152

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 4/11

3:20 pm-12:37 am

1 stop8h 17m

Chicago Midway

Mon 4/13

5:11 pm-11:58 pm

1 stop7h 47m

$155

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 4/16

1:09 pm-10:19 pm

1 stop8h 10m

Chicago Midway

Thu 4/23

6:00 am-12:09 pm

1 stop7h 09m

$159

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 5/8

1:09 pm-10:19 pm

1 stop8h 10m

Chicago Midway

Sat 5/9

2:20 pm-11:03 pm

1 stop9h 43m

$160

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 4/11

3:20 pm-12:37 am

1 stop8h 17m

Chicago Midway

Mon 4/13

6:00 am-12:09 pm

1 stop7h 09m

$161

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 4/15

1:09 pm-10:14 pm

1 stop8h 05m

Chicago Midway

Sat 4/18

6:00 am-12:14 pm

1 stop7h 14m

$162

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 5/1

8:00 am-9:37 pm

1 stop12h 37m

Chicago Midway

Mon 5/4

2:15 pm-10:29 pm

1 stop9h 14m

$164

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 4/25

11:59 pm-9:58 am

1 stop8h 59m

Chicago Midway

Tue 4/28

2:15 pm-10:29 pm

1 stop9h 14m

$165

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 4/9

6:25 pm-3:59 pm

1 stop20h 34m

Chicago Midway

Sun 4/12

4:46 pm-11:58 pm

1 stop8h 12m

$166

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 4/29

1:09 pm-10:14 pm

1 stop8h 05m

Chicago Midway

Sat 5/2

6:00 am-10:19 pm

2 stops17h 19m

$167

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Denver to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Denver, with most prices found around $177. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Denver during the month April is also very affordable. Most momondo users find prices during this month for around $197.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Denver. The lowest ticket price found for a Friday departure recently was $233. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Denver because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $303.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Denver in the evening is the least expensive time of day to depart. momondo users have found prices as low as $199 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $335. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Denver Intl to Chicago Midway flight route?

Fly from Denver Intl to Chicago Midway for the best Denver Intl - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Denver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $241 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Denver for as low as $196 on momondo.

What cabin class options are available on Denver Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on Denver Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Denver to Chicago Midway Airport flight prices changed over time?

As of March 2026, prices for Denver to Chicago Midway Airport flights are approximately 14% cheaper when compared to flights at the same time last year.

When to book flights from Denver to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Denver to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Denver to Chicago Midway Airport (DEN to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Denver to Chicago Midway Airport

Best Price Found

$193

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Denver in the past 72 hours is $193. The best round-trip flight deal from Denver to Chicago Midway Airport found on momondo in the last 72 hours is $283.
The fastest flight from Denver to Chicago Midway Airport takes 2h 20m
Direct flights go from Denver to Chicago Midway Airport every day.
Search flight deals

  • How far is Denver Intl to Chicago Midway by plane?

    Chicago Midway is 911.0 mi away from Denver Intl. 2h 20m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Denver Intl Airport to Chicago Midway Airport?

    Prices for flights from Denver Intl Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Denver Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Denver Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Denver Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Denver to Chicago Midway Airport?

  • What is the most popular airline from Denver to Chicago Midway Airport?

Best airlines flying from Denver to Chicago Midway Airport

Compare and see reviews for airlines that fly from Denver to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $78Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,308 reviews
Search Southwest flights

  • Southwest Flights From Denver to Chicago Midway Airport

    Across 15 Southwest flights from Denver to Chicago Midway Airport this week, the average price was $267, with the best Southwest deals starting from $157 round-trip. 4,307 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Denver to Chicago?

Finding the right flight to Chicago from Denver is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Denver to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Denver on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Denver to Chicago?

momondo helps you find the best flight between Denver and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Denver to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Denver are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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