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Cheap flights from Denver to Chicago from $65

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 2/21. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:43 am - 2:05 pm
DEN
-
MDW
2h 22mnonstop
Frontier Logo
3:00 pm - 4:49 pm
MDW
-
DEN
2h 49mnonstop
$96Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
7:26 pm - 10:56 pm
DEN
-
ORD
2h 30mnonstop
Frontier Logo
7:50 pm - 9:49 pm
ORD
-
DEN
2h 59mnonstop
$97Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
10:43 am - 2:05 pm
DEN
-
MDW
2h 22mnonstop
Frontier Logo
3:00 pm - 4:49 pm
MDW
-
DEN
2h 49mnonstop
$97Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
4:32 pm - 7:54 pm
DEN
-
MDW
2h 22mnonstop
Frontier Logo
9:09 pm - 10:59 pm
MDW
-
DEN
2h 50mnonstop
$105Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
7:26 pm - 10:56 pm
DEN
-
ORD
2h 30mnonstop
Frontier Logo
7:50 pm - 9:49 pm
ORD
-
DEN
2h 59mnonstop
$106Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
4:32 pm - 7:54 pm
DEN
-
MDW
2h 22mnonstop
Frontier Logo
9:09 pm - 10:59 pm
MDW
-
DEN
2h 50mnonstop
$106Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
7:35 pm - 11:14 pm
DEN
-
ORD
2h 39mnonstop
Frontier Logo
11:51 am - 9:35 pm
ORD
-
DEN
10h 44m1 stop
$107Frontier
Thu, Feb 12 - Wed, Feb 18
Frontier Logo
4:32 pm - 7:54 pm
DEN
-
MDW
2h 22mnonstop
Frontier Logo
9:09 pm - 10:59 pm
MDW
-
DEN
2h 50mnonstop
$107Frontier
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
9:44 pm - 1:15 pm
DEN
-
RFD
14h 31m1 stop
Multiple Airlines Logo
6:16 pm - 10:27 am
RFD
-
DEN
17h 11m1 stop
$205Multiple Airlines
Tue, Jan 20 - Fri, Jan 23
Multiple Airlines Logo
6:00 am - 5:26 pm
DEN
-
RFD
10h 26m1 stop
Multiple Airlines Logo
6:16 pm - 10:27 am
RFD
-
DEN
17h 11m1 stop
$257Multiple Airlines
Mon, Jan 19 - Fri, Jan 23

Frontier flights from Denver to Chicago

Our best Frontier deals on Denver to Chicago flight tickets
Frontier
Jan 9
DEN10:43 amDenver Intl
2h 22m
MDW2:05 pmChicago Midway
Jan 12
MDW3:00 pmChicago Midway
2h 49m
DEN4:49 pmDenver Intl
$96
Find similar
Frontier
Jan 9
DEN7:26 pmDenver Intl
2h 30m
ORD10:56 pmChicago O'Hare Intl
Jan 12
ORD7:50 pmChicago O'Hare Intl
2h 59m
DEN9:49 pmDenver Intl
$97
Find similar
Frontier
Jan 16
DEN4:32 pmDenver Intl
2h 22m
MDW7:54 pmChicago Midway
Jan 19
MDW9:09 pmChicago Midway
2h 50m
DEN10:59 pmDenver Intl
$105
Find similar

Southwest flights from Denver to Chicago

Our best Southwest deals on Denver to Chicago flight tickets
Southwest
Jan 14
DEN4:35 pmDenver Intl
2h 20m
MDW7:55 pmChicago Midway
Jan 18
MDW10:05 amChicago Midway
2h 45m
DEN11:50 amDenver Intl
$168
Find similar
Southwest
Jan 15
DEN7:40 amDenver Intl
2h 30m
MDW11:10 amChicago Midway
Jan 18
MDW2:10 pmChicago Midway
2h 40m
DEN3:50 pmDenver Intl
$176
Find similar
Southwest
Jan 14
DEN4:35 pmDenver Intl
2h 20m
MDW7:55 pmChicago Midway
Jan 18
MDW2:45 pmChicago Midway
5h 45m
1 stop
DEN7:30 pmDenver Intl
$178
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Denver to Chicago 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 20, 2025.
Use the filters below to find and compare flights from Denver to Chicago 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

Mon 1/12

3:00 pm-4:49 pm

Nonstop2h 49m

$96

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 1/9

7:26 pm-10:56 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 1/12

7:50 pm-9:49 pm

Nonstop2h 59m

$97

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

10:43 am-2:05 pm

Nonstop2h 22m

Chicago Midway

Mon 1/12

3:00 pm-4:49 pm

Nonstop2h 49m

$97

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/16

4:32 pm-7:54 pm

Nonstop2h 22m

Chicago Midway

Mon 1/19

9:09 pm-10:59 pm

Nonstop2h 50m

$105

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 1/9

7:26 pm-10:56 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 1/12

7:50 pm-9:49 pm

Nonstop2h 59m

$106

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/16

4:32 pm-7:54 pm

Nonstop2h 22m

Chicago Midway

Mon 1/19

9:09 pm-10:59 pm

Nonstop2h 50m

$106

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 2/12

7:35 pm-11:14 pm

Nonstop2h 39m

Chicago O'Hare Intl

Wed 2/18

11:51 am-9:35 pm

1 stop10h 44m

$107

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/16

4:32 pm-7:54 pm

Nonstop2h 22m

Chicago Midway

Mon 1/19

9:09 pm-10:59 pm

Nonstop2h 50m

$107

DenverChicago

DEN - RFD

DENRFD

Denver Intl

Tue 1/20

9:44 pm-1:15 pm

1 stop14h 31m

Chicago Greater Rockford

Fri 1/23

6:16 pm-10:27 am

1 stop17h 11m

$205

DenverChicago

DEN - RFD

DENRFD

Denver Intl

Mon 1/19

6:00 am-5:26 pm

1 stop10h 26m

Chicago Greater Rockford

Fri 1/23

6:16 pm-10:27 am

1 stop17h 11m

$257

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

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?

The month of January is, on average, the cheapest month to fly to Chicago from Denver, with most prices found around $181. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Denver to Chicago during February average around $185.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $302. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Denver to Chicago for around $517.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Denver to Chicago during this time can be as low as $199. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $621.

What is the cheapest Denver Intl to Chicago flight route?

Fly from Denver Intl to Chicago O'Hare Intl for the best Denver Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Denver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $242 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Denver for as low as $201 on momondo.

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

There are 4 cabin classes available to choose from on Denver Intl to Chicago 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 flights?

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

How have Denver to Chicago flight prices changed over time?

As of December 2025, prices for Denver to Chicago flights are approximately 41% more expensive when compared to flights at the same time last year.

When to book flights from Denver to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Denver to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Denver to Chicago (DEN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Denver to Chicago

Best Price Found

$134

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Denver in the past 72 hours is $134. The best round-trip flight deal from Denver to Chicago found on momondo in the last 72 hours is $180.
The fastest flight from Denver to Chicago takes 2h 15m
Direct flights go from Denver to Chicago every day.
There are 3 airports in Chicago. From Denver there are direct flights to Chicago Midway (MDW).
Search flight deals

  • How far is Denver Intl to Chicago by plane?

    There are 917.4 mi between Denver Intl and Chicago. 2h 15m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Denver Intl Airport to Chicago?

    Prices for flights from Denver Intl Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Denver Intl Airport to Chicago?

  • How old do you have to be to fly from Denver Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Denver Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Denver to Chicago?

  • What is the most popular airline from Denver to Chicago?

Best airlines flying from Denver to Chicago

Compare and see reviews for airlines that fly from Denver to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $64Free CancellationRating
5.8
3,082 reviews
Search Frontier flights
American AirlinesPriceFrom $156Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,258 reviews
Search Southwest flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,096 reviews
Search United Airlines flights

  • Southwest Flights From Denver to Chicago

    The lowest priced Southwest flight from Denver to Chicago from the last 72 hours was $156. Generally, Southwest has 60 flights on this route every week with an average price of $261. Southwest is rated 8.0/10 by our users.

  • United Airlines Flights From Denver to Chicago

    Across 9,096 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Denver to Chicago about 55 times each week, with ticket deals ranging from $163 to $294. Price data is based on momondo 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
Valparaiso
Schererville
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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Denver to Chicago for you.

Can I find flights from Denver to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Denver with this policy.

How can momondo help me find flights from Denver to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Denver.

I’m not ready to book a flight from Denver to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Denver and alert you when they change.

An easier way to manage your Chicago 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.
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport