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Cheap flights from Denver to Chicago from $103

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 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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.
Southwest Logo
7:15 am - 10:35 am
DEN
-
MDW
2h 20mnonstop
Southwest Logo
6:00 pm - 7:40 pm
MDW
-
DEN
2h 40mnonstop
$205Southwest
Sat, Aug 22 - Tue, Aug 25
Southwest Logo
4:55 pm - 8:15 pm
DEN
-
MDW
2h 20mnonstop
Southwest Logo
8:15 pm - 9:50 pm
MDW
-
DEN
2h 35mnonstop
$210Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
11:10 am - 5:10 pm
DEN
-
MDW
5h 00m
1 stop
Southwest Logo
6:00 pm - 7:40 pm
MDW
-
DEN
2h 40mnonstop
$211Southwest
Sat, Aug 22 - Sat, Sep 5
Southwest Logo
11:05 am - 4:00 pm
DEN
-
MDW
3h 55m
1 stop
Southwest Logo
8:15 pm - 9:50 pm
MDW
-
DEN
2h 35mnonstop
$215Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
4:55 pm - 8:15 pm
DEN
-
MDW
2h 20mnonstop
Southwest Logo
2:15 pm - 6:30 pm
MDW
-
DEN
5h 15m
1 stop
$216Southwest
Fri, Sep 11 - Sat, Sep 12
Southwest Logo
12:30 pm - 6:00 pm
DEN
-
MDW
4h 30m
1 stop
Southwest Logo
11:05 am - 3:45 pm
MDW
-
DEN
5h 40m
1 stop
$220Southwest
Sat, Oct 3 - Mon, Oct 5
Southwest Logo
11:10 am - 5:10 pm
DEN
-
MDW
5h 00m
1 stop
Southwest Logo
1:55 pm - 7:50 pm
MDW
-
DEN
6h 55m
2 stops
$221Southwest
Sat, Aug 15 - Tue, Aug 18
Southwest Logo
8:25 pm - 11:45 pm
DEN
-
MDW
2h 20mnonstop
Southwest Logo
9:00 am - 12:55 pm
MDW
-
DEN
4h 55m
1 stop
$222Southwest
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
11:00 am - 5:00 pm
DEN
-
MDW
5h 00m
1 stop
Southwest Logo
6:20 am - 9:20 am
MDW
-
DEN
4h 00m
1 stop
$225Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
11:10 am - 7:10 pm
DEN
-
MDW
7h 00m
2 stops
Southwest Logo
9:00 am - 12:55 pm
MDW
-
DEN
4h 55m
1 stop
$226Southwest
Sat, Aug 22 - Wed, Aug 26

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Delta flights from Denver to Chicago Midway Airport

Our best Delta deals on Denver to Chicago Midway Airport flight tickets
Delta
Aug 25
DEN6:05 amDenver Intl
5h 34m
1 stop
MDW12:39 pmChicago Midway
Sep 8
MDW7:13 pmChicago Midway
5h 22m
1 stop
DEN11:35 pmDenver Intl
$235
Delta
Sep 5
DEN10:19 amDenver Intl
5h 40m
1 stop
MDW4:59 pmChicago Midway
Sep 9
MDW7:13 pmChicago Midway
5h 22m
1 stop
DEN11:35 pmDenver Intl
$236
Delta
Aug 12
DEN6:05 amDenver Intl
5h 34m
1 stop
MDW12:39 pmChicago Midway
Aug 17
MDW1:25 pmChicago Midway
4h 58m
1 stop
DEN5:23 pmDenver Intl
$247

Southwest flights from Denver to Chicago Midway Airport

Our best Southwest deals on Denver to Chicago Midway Airport flight tickets
Southwest
Sep 10
DEN6:30 pmDenver Intl
2h 30m
MDW10:00 pmChicago Midway
Sep 14
MDW8:15 pmChicago Midway
2h 35m
DEN9:50 pmDenver Intl
$205
Southwest
Sep 2
DEN7:25 pmDenver Intl
2h 25m
MDW10:50 pmChicago Midway
Sep 6
MDW8:25 amChicago Midway
2h 45m
DEN10:10 amDenver Intl
$210
Southwest
Oct 3
DEN12:30 pmDenver Intl
4h 30m
1 stop
MDW6:00 pmChicago Midway
Oct 5
MDW8:45 amChicago Midway
2h 40m
DEN10:25 amDenver Intl
$211

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 July 23, 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

Sat 8/22

7:15 am-10:35 am

Nonstop2h 20m

Chicago Midway

Tue 8/25

6:00 pm-7:40 pm

Nonstop2h 40m

$205
Quickest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/11

4:55 pm-8:15 pm

Nonstop2h 20m

Chicago Midway

Mon 9/14

8:15 pm-9:50 pm

Nonstop2h 35m

$210

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 8/22

11:10 am-5:10 pm

1 stop5h 00m

Chicago Midway

Sat 9/5

6:00 pm-7:40 pm

Nonstop2h 40m

$211

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 9/10

11:05 am-4:00 pm

1 stop3h 55m

Chicago Midway

Mon 9/14

8:15 pm-9:50 pm

Nonstop2h 35m

$215

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/11

4:55 pm-8:15 pm

Nonstop2h 20m

Chicago Midway

Sat 9/12

2:15 pm-6:30 pm

1 stop5h 15m

$216

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/3

12:30 pm-6:00 pm

1 stop4h 30m

Chicago Midway

Mon 10/5

11:05 am-3:45 pm

1 stop5h 40m

$220

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 8/15

11:10 am-5:10 pm

1 stop5h 00m

Chicago Midway

Tue 8/18

1:55 pm-7:50 pm

2 stops6h 55m

$221

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/11

8:25 pm-11:45 pm

Nonstop2h 20m

Chicago Midway

Tue 9/15

9:00 am-12:55 pm

1 stop4h 55m

$222

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 9/10

11:00 am-5:00 pm

1 stop5h 00m

Chicago Midway

Mon 9/14

6:20 am-9:20 am

1 stop4h 00m

$225

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 8/22

11:10 am-7:10 pm

2 stops7h 00m

Chicago Midway

Wed 8/26

9:00 am-12:55 pm

1 stop4h 55m

$226

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 November is, on average, the cheapest month to fly to Chicago Midway Airport from Denver, with most prices found around $218. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Denver during the month December is also very affordable. Most momondo users find prices during this month for around $222.

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 $276. 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 $431.

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 $265 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $398. 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 $302 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 July 2026, prices for Denver to Chicago Midway Airport flights are approximately 229% 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

$213

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 $213. The best round-trip flight deal from Denver to Chicago Midway Airport found on momondo in the last 72 hours is $287.
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 $86Free CancellationRating
5.6
2,770 reviews
Search Frontier flights
SouthwestPriceFrom $185Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

  • Southwest Flights From Denver to Chicago Midway Airport

    Across 56 Southwest flights from Denver to Chicago Midway Airport this week, the average price was $349, with the best Southwest deals starting from $185 round-trip. 4,240 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
Crown Point
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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