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Cheap flights from Denver to Chicago from $58

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 12/30. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:43 am - 2:05 pmDEN-MDW
2h 22mnonstop
Frontier Logo
6:10 am - 8:20 pmMDW-DEN
15h 10m1 stop
$107Frontier
Find Deal
Fri, Jan 9 - Sat, Jan 10
Frontier Logo
1:42 pm - 10:17 pmDEN-MDW
7h 35m1 stop
Frontier Logo
3:00 pm - 4:49 pmMDW-DEN
2h 49mnonstop
$109Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
10:43 am - 2:05 pmDEN-MDW
2h 22mnonstop
Frontier Logo
6:10 am - 12:21 pmMDW-DEN
7h 11m1 stop
$110Frontier
Find Deal
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
10:43 am - 2:05 pmDEN-MDW
2h 22mnonstop
Frontier Logo
3:01 pm - 11:59 amMDW-DEN
21h 58m1 stop
$116Frontier
Find Deal
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
4:36 pm - 7:55 pmDEN-MDW
2h 19mnonstop
Frontier Logo
10:50 pm - 12:45 amMDW-DEN
2h 55mnonstop
$121Frontier
Find Deal
Tue, Dec 30 - Sun, Jan 4
Frontier Logo
12:05 am - 10:31 amDEN-MDW
9h 26m1 stop
Frontier Logo
11:05 am - 7:53 amMDW-DEN
21h 48m1 stop
$122Frontier
Find Deal
Tue, Jan 13 - Sun, Jan 18
Frontier Logo
7:00 am - 8:45 pmDEN-MDW
12h 45m1 stop
Frontier Logo
3:05 pm - 4:54 pmMDW-DEN
2h 49mnonstop
$123Frontier
Find Deal
Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
10:43 am - 2:05 pmDEN-MDW
2h 22mnonstop
Multiple Airlines Logo
3:01 pm - 10:20 amMDW-DEN
20h 19m2 stops
$127Multiple Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
12:05 am - 10:34 amDEN-MDW
9h 29m1 stop
Frontier Logo
6:10 am - 12:21 pmMDW-DEN
7h 11m1 stop
$128Frontier
Find Deal
Mon, Jan 12 - Wed, Jan 14
Frontier Logo
10:43 am - 2:05 pmDEN-MDW
2h 22mnonstop
Frontier Logo
6:10 am - 8:02 pmMDW-DEN
14h 52m2 stops
$130Frontier
Find Deal
Fri, Jan 9 - Sun, Jan 11

Frontier flights from Denver to Chicago Midway Airport

Our best Frontier deals on Denver to Chicago Midway Airport flight tickets
Frontier
Jan 9
DEN10:43 amDenver Intl
2h 22m
MDW2:05 pmChicago Midway
Jan 10
MDW6:10 amChicago Midway
15h 10m
1 stop
DEN8:20 pmDenver Intl
$107
Find similar
Frontier
Jan 8
DEN1:42 pmDenver Intl
7h 35m
1 stop
MDW10:17 pmChicago Midway
Jan 12
MDW3:00 pmChicago Midway
2h 49m
DEN4:49 pmDenver Intl
$109
Find similar
Frontier
Jan 9
DEN10:43 amDenver Intl
2h 22m
MDW2:05 pmChicago Midway
Jan 12
MDW6:10 amChicago Midway
7h 11m
1 stop
DEN12:21 pmDenver Intl
$110
Find similar

Southwest flights from Denver to Chicago Midway Airport

Our best Southwest deals on Denver to Chicago Midway Airport flight tickets
Southwest
Jan 20
DEN7:00 amDenver Intl
6h 15m
1 stop
MDW2:15 pmChicago Midway
Jan 24
MDW7:40 pmChicago Midway
2h 45m
DEN9:25 pmDenver Intl
$139
Find similar
Southwest
Jan 11
DEN7:40 amDenver Intl
2h 30m
MDW11:10 amChicago Midway
Jan 18
MDW7:55 pmChicago Midway
2h 45m
DEN9:40 pmDenver Intl
$176
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 December 1, 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

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Sat 1/10

6:10 am-8:20 pm

1 stop15h 10m

$107

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 1/8

1:42 pm-10:17 pm

1 stop7h 35m

Chicago Midway

Mon 1/12

3:00 pm-4:49 pm

Nonstop2h 49m

$109

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Mon 1/12

6:10 am-12:21 pm

1 stop7h 11m

$110

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Mon 1/12

3:01 pm-11:59 am

1 stop21h 58m

$116

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 12/30

4:36 pm-7:55 pm

Nonstop2h 19m

Chicago Midway

Sun 1/4

10:50 pm-12:45 am

Nonstop2h 55m

$121

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 1/13

12:05 am-10:31 am

1 stop9h 26m

Chicago Midway

Sun 1/18

11:05 am-7:53 am

1 stop21h 48m

$122

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 1/5

7:00 am-8:45 pm

1 stop12h 45m

Chicago Midway

Fri 1/9

3:05 pm-4:54 pm

Nonstop2h 49m

$123

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Mon 1/12

3:01 pm-10:20 am

2 stops20h 19m

$127

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 1/12

12:05 am-10:34 am

1 stop9h 29m

Chicago Midway

Wed 1/14

6:10 am-12:21 pm

1 stop7h 11m

$128

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Sun 1/11

6:10 am-8:02 pm

2 stops14h 52m

$130

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 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 $177.

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 $227. 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, Saturday 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 $302.

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 $177 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $327. 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 $223 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 $181 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 December 2025, prices for Denver to Chicago Midway Airport flights are approximately 19% 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

$120

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 $120. The best round-trip flight deal from Denver to Chicago Midway Airport found on momondo in the last 72 hours is $153.
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 19m 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 $67Free CancellationRating
5.8
3,094 reviews
Search Frontier flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

  • Southwest Flights From Denver to Chicago Midway Airport

    Across 12 Southwest flights from Denver to Chicago Midway Airport this week, the average price was $257, with the best Southwest deals starting from $157 round-trip. 4,253 users have rated Southwest on momondo, with an average score of 8.0/10.

  • Frontier Flights From Denver to Chicago Midway Airport

    Frontier (5.8/10 from 3,094 reviews) operates around 1 flight from Denver to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $172, with deals from around $67 rare but found on momondo. Referenced prices are for round-trip Denver to Chicago Midway Airport flight searches in the last 72 hours.

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
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

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