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Cheap flights from Denver to Chicago from $89

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 5/2. 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
10:00 am - 11:09 am
DEN
-
MDW
24h 09m
2 stops
Frontier Logo
3:07 pm - 6:33 am
MDW
-
DEN
16h 26m
1 stop
$182Frontier
Tue, May 12 - Tue, May 19
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
6:00 am - 2:04 pm
MDW
-
DEN
9h 04m
1 stop
$185Frontier
Tue, May 26 - Thu, May 28
Frontier Logo
1:09 pm - 10:14 pm
DEN
-
MDW
8h 05m
1 stop
Frontier Logo
2:15 pm - 10:29 pm
MDW
-
DEN
9h 14m
1 stop
$186Frontier
Sat, May 2 - Mon, May 4
Delta Logo
6:05 am - 12:42 pm
DEN
-
MDW
5h 37m
1 stop
Delta Logo
9:22 am - 1:59 pm
MDW
-
DEN
5h 37m
1 stop
$187Delta
Thu, May 7 - Tue, May 19
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
4:52 pm - 11:11 pm
MDW
-
DEN
31h 19m
1 stop
$192Frontier
Sat, May 16 - Mon, May 18
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
3:07 pm - 9:09 pm
MDW
-
DEN
7h 02m
1 stop
$193Frontier
Wed, May 6 - Mon, May 11
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
12:04 pm - 10:24 pm
MDW
-
DEN
11h 20m
1 stop
$194Frontier
Wed, May 6 - Wed, May 20
Frontier Logo
5:05 am - 2:12 pm
DEN
-
MDW
8h 07m
1 stop
Frontier Logo
11:59 am - 10:24 pm
MDW
-
DEN
11h 25m
1 stop
$196Frontier
Thu, May 21 - Sat, May 23
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
12:04 pm - 10:24 pm
MDW
-
DEN
11h 20m
1 stop
$198Frontier
Tue, May 5 - Fri, May 8
Frontier Logo
11:54 pm - 11:04 am
DEN
-
MDW
10h 10m
1 stop
Frontier Logo
4:52 pm - 11:11 pm
MDW
-
DEN
31h 19m
1 stop
$199Frontier
Fri, May 15 - Mon, May 18

Southwest flights from Denver to Chicago Midway Airport

Our best Southwest deals on Denver to Chicago Midway Airport flight tickets
Southwest
May 9
DEN6:30 amDenver Intl
2h 20m
MDW9:50 amChicago Midway
May 13
MDW11:35 amChicago Midway
5h 45m
1 stop
DEN4:20 pmDenver Intl
$202
Southwest
May 16
DEN6:30 amDenver Intl
2h 20m
MDW9:50 amChicago Midway
May 19
MDW8:50 pmChicago Midway
2h 45m
DEN10:35 pmDenver Intl
$209
Southwest
May 6
DEN6:35 amDenver Intl
2h 20m
MDW9:55 amChicago Midway
May 9
MDW5:30 pmChicago Midway
2h 40m
DEN7:10 pmDenver Intl
$211

Frontier flights from Denver to Chicago Midway Airport

Our best Frontier deals on Denver to Chicago Midway Airport flight tickets
Frontier
May 12
DEN10:00 amDenver Intl
24h 09m
2 stops
MDW11:09 amChicago Midway
May 19
MDW3:07 pmChicago Midway
16h 26m
1 stop
DEN6:33 amDenver Intl
$182
Frontier
May 26
DEN11:54 pmDenver Intl
10h 15m
1 stop
MDW11:09 amChicago Midway
May 28
MDW6:00 amChicago Midway
9h 04m
1 stop
DEN2:04 pmDenver Intl
$185
Frontier
May 2
DEN1:09 pmDenver Intl
8h 05m
1 stop
MDW10:14 pmChicago Midway
May 4
MDW2:15 pmChicago Midway
9h 14m
1 stop
DEN10:29 pmDenver Intl
$186

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 April 18, 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

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 5/12

10:00 am-11:09 am

2 stops24h 09m

Chicago Midway

Tue 5/19

3:07 pm-6:33 am

1 stop16h 26m

$182

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 5/26

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Thu 5/28

6:00 am-2:04 pm

1 stop9h 04m

$185

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 5/2

1:09 pm-10:14 pm

1 stop8h 05m

Chicago Midway

Mon 5/4

2:15 pm-10:29 pm

1 stop9h 14m

$186
Quickest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/7

6:05 am-12:42 pm

1 stop5h 37m

Chicago Midway

Tue 5/19

9:22 am-1:59 pm

1 stop5h 37m

$187

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 5/16

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Mon 5/18

4:52 pm-11:11 pm

1 stop31h 19m

$192

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 5/6

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Mon 5/11

3:07 pm-9:09 pm

1 stop7h 02m

$193

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 5/6

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Wed 5/20

12:04 pm-10:24 pm

1 stop11h 20m

$194

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/21

5:05 am-2:12 pm

1 stop8h 07m

Chicago Midway

Sat 5/23

11:59 am-10:24 pm

1 stop11h 25m

$196

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 5/5

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Fri 5/8

12:04 pm-10:24 pm

1 stop11h 20m

$198

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 5/15

11:54 pm-11:04 am

1 stop10h 10m

Chicago Midway

Mon 5/18

4:52 pm-11:11 pm

1 stop31h 19m

$199

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 typical price of a round-trip flight between Denver and Chicago Midway Airport?

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 November is also very affordable. Most momondo users find prices during this month for around $220.

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 $241. 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 $338.

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 $238 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $352. 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 $262 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 $188 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.

Can stopping save me money on Denver to Chicago Midway Airport flights?

You could potentially save up to 7% on your flight if you consider stops on a Denver to Chicago Midway Airport flight.

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

As of April 2026, prices for Denver to Chicago Midway Airport flights are approximately 234% more expensive 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

$178

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 $178. The best round-trip flight deal from Denver to Chicago Midway Airport found on momondo in the last 72 hours is $307.
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

Frequently asked questions about flying from Denver to Chicago Midway Airport

  • 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 $107Free CancellationRating
5.7
2,987 reviews
Search Frontier flights
SouthwestPriceFrom $160Free CancellationRating
8.0
4,328 reviews
Search Southwest flights

  • Southwest Flights From Denver to Chicago Midway Airport

    Across 27 Southwest flights from Denver to Chicago Midway Airport this week, the average price was $276, with the best Southwest deals starting from $160 round-trip. 4,330 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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