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Cheap flights from Denver to Chicago from $107

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Denver to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:05 am - 2:35 pmDEN  Denver Intl-MDW Chicago Midway
7h 30m1 stop Dallas/Fort Worth
Frontier Logo
12:20 pm - 9:42 pmMDW  Chicago Midway-DEN Denver Intl
10h 22m1 stop Dallas/Fort Worth
$190Frontier
Sat, Oct 24 - Sat, Oct 31
Frontier Logo
10:44 am - 5:46 pmDEN  Denver Intl-MDW Chicago Midway
6h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:30 pm - 9:49 pmMDW  Chicago Midway-DEN Denver Intl
7h 19m1 stop Dallas/Fort Worth
$190Frontier
Tue, Oct 6 - Sat, Oct 10
Southwest Logo
7:50 pm - 11:15 pmDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
6:05 am - 7:45 amMDW  Chicago Midway-DEN Denver Intl
2h 40mnonstop
$190Southwest
Wed, Oct 14 - Tue, Oct 20
Frontier Logo
6:25 am - 7:47 pmDEN  Denver Intl-MDW Chicago Midway
12h 22m1 stop Orlando
Frontier Logo
2:04 pm - 9:19 pmMDW  Chicago Midway-DEN Denver Intl
8h 15m1 stop Atlanta Hartsfield-Jackson
$190Frontier
Thu, Nov 26 - Thu, Dec 3
Frontier Logo
10:41 am - 5:47 pmDEN  Denver Intl-MDW Chicago Midway
6h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:42 pm - 6:36 amMDW  Chicago Midway-DEN Denver Intl
12h 54m1 stop Atlanta Hartsfield-Jackson
$190Frontier
Tue, Nov 17 - Thu, Nov 19
Southwest Logo
11:00 am - 4:05 pmDEN  Denver Intl-MDW Chicago Midway
4h 05m1 stop Wichita Eisenhower National
Southwest Logo
7:20 pm - 9:00 pmMDW  Chicago Midway-DEN Denver Intl
2h 40mnonstop
$195Southwest
Wed, Oct 14 - Tue, Oct 20
Southwest Logo
7:50 pm - 11:15 pmDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
7:25 pm - 9:10 pmMDW  Chicago Midway-DEN Denver Intl
2h 45mnonstop
$196Southwest
Tue, Oct 20 - Sat, Oct 24
Delta Logo
6:10 am - 11:51 amDEN  Denver Intl-MDW Chicago Midway
4h 41m1 stop Minneapolis St Paul
Delta Logo
1:00 pm - 5:30 pmMDW  Chicago Midway-DEN Denver Intl
5h 30m1 stop Detroit Metropolitan Wayne County
$249Delta
Thu, Feb 25 - Mon, Mar 1
Delta Logo
6:45 am - 12:33 pmDEN  Denver Intl-MDW Chicago Midway
4h 48m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 2:03 pmMDW  Chicago Midway-DEN Denver Intl
5h 33m1 stop Detroit Metropolitan Wayne County
$249Delta
Mon, Feb 22 - Tue, Mar 2
Delta Logo
6:45 am - 12:33 pmDEN  Denver Intl-MDW Chicago Midway
4h 48m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:55 am - 3:56 pmMDW  Chicago Midway-DEN Denver Intl
7h 01m1 stop Minneapolis St Paul
$249Delta
Mon, Feb 22 - Mon, Mar 1

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Frontier flights from Denver to Chicago Midway Airport

Our best Frontier deals on Denver to Chicago Midway Airport flight tickets
Frontier
Nov 26
DEN6:25 amDenver Intl
12h 22m
1 stop
MDW7:47 pmChicago Midway
Dec 3
MDW2:04 pmChicago Midway
8h 15m
1 stop
DEN9:19 pmDenver Intl
$190
Frontier
Oct 6
DEN10:44 amDenver Intl
6h 02m
1 stop
MDW5:46 pmChicago Midway
Oct 10
MDW3:30 pmChicago Midway
7h 19m
1 stop
DEN9:49 pmDenver Intl
$193
Frontier
Oct 30
DEN10:41 amDenver Intl
12h 06m
1 stop
MDW11:47 pmChicago Midway
Nov 3
MDW12:27 pmChicago Midway
10h 15m
1 stop
DEN9:42 pmDenver Intl
$204

Southwest flights from Denver to Chicago Midway Airport

Our best Southwest deals on Denver to Chicago Midway Airport flight tickets
Southwest
Oct 14
DEN11:00 amDenver Intl
4h 05m
1 stop
MDW4:05 pmChicago Midway
Oct 20
MDW7:20 pmChicago Midway
2h 40m
DEN9:00 pmDenver Intl
$195
Southwest
Oct 20
DEN7:50 pmDenver Intl
2h 25m
MDW11:15 pmChicago Midway
Oct 24
MDW7:25 pmChicago Midway
2h 45m
DEN9:10 pmDenver Intl
$196
Southwest
Oct 14
DEN11:00 amDenver Intl
4h 05m
1 stop
MDW4:05 pmChicago Midway
Oct 20
MDW1:05 pmChicago Midway
4h 50m
1 stop
DEN4:55 pmDenver Intl
$200

momondo Fare Finder

 
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 Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Sat 10/24

6:05 am-2:35 pm

1 stop7h 30m

Chicago Midway

Sat 10/31

12:20 pm-9:42 pm

1 stop10h 22m

$190

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Tue 10/6

10:44 am-5:46 pm

1 stop6h 02m

Chicago Midway

Sat 10/10

3:30 pm-9:49 pm

1 stop7h 19m

$190
Quickest round-trip

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Wed 10/14

7:50 pm-11:15 pm

Nonstop2h 25m

Chicago Midway

Tue 10/20

6:05 am-7:45 am

Nonstop2h 40m

$190

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Thu 11/26

6:25 am-7:47 pm

1 stop12h 22m

Chicago Midway

Thu 12/3

2:04 pm-9:19 pm

1 stop8h 15m

$190

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Tue 11/17

10:41 am-5:47 pm

1 stop6h 06m

Chicago Midway

Thu 11/19

6:42 pm-6:36 am

1 stop12h 54m

$190

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Wed 10/14

11:00 am-4:05 pm

1 stop4h 05m

Chicago Midway

Tue 10/20

7:20 pm-9:00 pm

Nonstop2h 40m

$195

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Tue 10/20

7:50 pm-11:15 pm

Nonstop2h 25m

Chicago Midway

Sat 10/24

7:25 pm-9:10 pm

Nonstop2h 45m

$196

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Thu 2/25

6:10 am-11:51 am

1 stop4h 41m

Chicago Midway

Mon 3/1

1:00 pm-5:30 pm

1 stop5h 30m

$249

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Mon 2/22

6:45 am-12:33 pm

1 stop4h 48m

Chicago Midway

Tue 3/2

9:30 am-2:03 pm

1 stop5h 33m

$249

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Mon 2/22

6:45 am-12:33 pm

1 stop4h 48m

Chicago Midway

Mon 3/1

9:55 am-3:56 pm

1 stop7h 01m

$249

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?

Prices are currently low for flights on this route.

Typical prices usually range from $285 to $437.
The lowest price recently found on this route was $190.

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

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Denver, with most prices found around $206. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Denver during the month November is also very affordable. Most momondo users find prices during this month for around $218.

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 $298. 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 $449.

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 $287 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $427. 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 from Denver 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 $316 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 $217 on momondo.

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

There is only 1 cabin class available to choose from on Denver to Chicago Midway Airport 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?

No. A direct flight is the cheapest option for a flight between Denver to Chicago Midway Airport.

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

As of September 2026, prices for Denver to Chicago Midway Airport flights are approximately 135% 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

$107

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Denver in the past 72 hours is $107. The best round-trip flight deal from Denver to Chicago Midway Airport found on momondo in the last 72 hours is $190.
The fastest flight from Denver to Chicago Midway Airport takes 2h 15m
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 15m 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 $100Free CancellationRating
5.6
2,601 reviews
Search Frontier flights
SouthwestPriceFrom $201Free CancellationRating
8.0
4,190 reviews
Search Southwest flights

  • Southwest Flights From Denver to Chicago Midway Airport

    Across 49 Southwest flights from Denver to Chicago Midway Airport this week, the average price was $362, with the best Southwest deals starting from $201 round-trip. 4,190 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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