Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Denver to Chicago from $59

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 9/26. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Denver to Chicago

Cheap round-trip flights

Frontier Logo
9:12 pm - 12:36 amDEN-MDW
2h 24mnonstop
Frontier Logo
12:30 pm - 2:16 pmMDW-DEN
2h 46mnonstop
$109Frontier
Find Deal
Thu, Oct 23 - Thu, Oct 30
Frontier Logo
8:05 am - 11:30 amDEN-MDW
2h 25mnonstop
Frontier Logo
12:30 pm - 2:16 pmMDW-DEN
2h 46mnonstop
$110Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
7:49 am - 11:16 amDEN-MDW
2h 27mnonstop
Frontier Logo
12:11 pm - 1:57 pmMDW-DEN
2h 46mnonstop
$111Frontier
Find Deal
Fri, Oct 24 - Mon, Oct 27
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
Frontier Logo
4:48 pm - 6:26 pmMDW-DEN
2h 38mnonstop
$113Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
7:49 am - 11:16 amDEN-MDW
2h 27mnonstop
Frontier Logo
6:24 pm - 8:08 pmMDW-DEN
2h 44mnonstop
$114Frontier
Find Deal
Fri, Oct 24 - Sun, Oct 26
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
Frontier Logo
6:30 am - 10:53 pmMDW-DEN
17h 23m1 stop
$115Frontier
Find Deal
Fri, Sep 5 - Sun, Sep 7
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
Frontier Logo
2:26 pm - 10:53 pmMDW-DEN
9h 27m1 stop
$116Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
9:12 pm - 12:36 amDEN-MDW
2h 24mnonstop
Frontier Logo
6:24 pm - 8:08 pmMDW-DEN
2h 44mnonstop
$118Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
7:40 am - 8:46 pmDEN-MDW
12h 06m1 stop
Frontier Logo
4:48 pm - 6:26 pmMDW-DEN
2h 38mnonstop
$119Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Southwest Logo
8:15 pm - 11:30 pmDEN-MDW
2h 15mnonstop
Southwest Logo
9:50 pm - 11:25 pmMDW-DEN
2h 35mnonstop
$163Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6

Frontier flights from Denver to Chicago Midway Airport

Our best Frontier deals on Denver to Chicago Midway Airport flight tickets
Frontier
Oct 23
DEN9:12 pmDenver Intl
2h 24m
MDW12:36 amChicago Midway
Oct 30
MDW12:30 pmChicago Midway
2h 46m
DEN2:16 pmDenver Intl
$109
Find similar
Frontier
Nov 13
DEN8:05 amDenver Intl
2h 25m
MDW11:30 amChicago Midway
Nov 17
MDW12:30 pmChicago Midway
2h 46m
DEN2:16 pmDenver Intl
$110
Find similar
Frontier
Oct 24
DEN7:49 amDenver Intl
2h 27m
MDW11:16 amChicago Midway
Oct 27
MDW12:11 pmChicago Midway
2h 46m
DEN1:57 pmDenver Intl
$111
Find similar

Southwest flights from Denver to Chicago Midway Airport

Our best Southwest deals on Denver to Chicago Midway Airport flight tickets
Southwest
Oct 2
DEN8:15 pmDenver Intl
2h 15m
MDW11:30 pmChicago Midway
Oct 6
MDW9:50 pmChicago Midway
2h 35m
DEN11:25 pmDenver Intl
$163
Find similar
Southwest
Sep 3
DEN1:10 pmDenver Intl
2h 20m
MDW4:30 pmChicago Midway
Sep 4
MDW3:20 pmChicago Midway
2h 35m
DEN4:55 pmDenver Intl
$179
Find similar
Southwest
Sep 6
DEN1:10 pmDenver Intl
2h 20m
MDW4:30 pmChicago Midway
Sep 9
MDW6:00 amChicago Midway
2h 35m
DEN7:35 amDenver Intl
$204
Find similar

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 August 26, 2025.
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

Thu 10/23

9:12 pm-12:36 am

Nonstop2h 24m

Chicago Midway

Thu 10/30

12:30 pm-2:16 pm

Nonstop2h 46m

$109

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 11/13

8:05 am-11:30 am

Nonstop2h 25m

Chicago Midway

Mon 11/17

12:30 pm-2:16 pm

Nonstop2h 46m

$110

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 10/24

7:49 am-11:16 am

Nonstop2h 27m

Chicago Midway

Mon 10/27

12:11 pm-1:57 pm

Nonstop2h 46m

$111

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/12

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Mon 9/15

4:48 pm-6:26 pm

Nonstop2h 38m

$113

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 10/24

7:49 am-11:16 am

Nonstop2h 27m

Chicago Midway

Sun 10/26

6:24 pm-8:08 pm

Nonstop2h 44m

$114

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/5

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Sun 9/7

6:30 am-10:53 pm

1 stop17h 23m

$115

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/5

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Mon 9/8

2:26 pm-10:53 pm

1 stop9h 27m

$116

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 10/16

9:12 pm-12:36 am

Nonstop2h 24m

Chicago Midway

Mon 10/20

6:24 pm-8:08 pm

Nonstop2h 44m

$118

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/12

7:40 am-8:46 pm

1 stop12h 06m

Chicago Midway

Mon 9/15

4:48 pm-6:26 pm

Nonstop2h 38m

$119

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 10/2

8:15 pm-11:30 pm

Nonstop2h 15m

Chicago Midway

Mon 10/6

9:50 pm-11:25 pm

Nonstop2h 35m

$163

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Denver, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Denver during the month September is also very affordable. Most momondo users find prices during this month for around $163.

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 $208. 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 $279.

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 $170 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $312. 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 $213 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 $158 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 August 2025, prices for Denver to Chicago Midway Airport flights are approximately 15% 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

$128

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 $128. The best round-trip flight deal from Denver to Chicago Midway Airport found on momondo in the last 72 hours is $166.
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

  • 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 $65Free CancellationRating
5.8
3,200 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,243 reviews
Search Southwest flights
American AirlinesPriceFrom $195Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Southwest Flights From Denver to Chicago Midway Airport

    Across 41 Southwest flights from Denver to Chicago Midway Airport this week, the average price was $251, with the best Southwest deals starting from $159 round-trip. 4,243 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 8/31
Sun 9/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago