$45 Cheap Flights from Denver (DEN) to Chicago (CHI)

View $45 flight on Sat, Sep 27, 2025Opens in a new window

Popular airlines from Denver Intl. Airport (DEN) to Chicago

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Today's featured flight deals from Denver Intl. Airport (DEN) to Chicago

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Denver to Chicago (DEN-CHI)

Prices were available within the past 7 days and start at $45 for one-way flights and $80 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Sep 27 - Wed, Oct 1
DEN
Denver
ORD
Chicago
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 27 from Denver to Chicago, returning Wed, Oct 1, priced at $80 just found
Frontier Airlines
Tue, Sep 9 - Tue, Sep 16
DEN
Denver
ORD
Chicago
$90 Roundtrip, found 9 hours ago
$90
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Sep 9 from Denver to Chicago, returning Tue, Sep 16, priced at $90 found 9 hours ago
Frontier Airlines
Mon, Oct 20 - Wed, Oct 22
DEN
Denver
ORD
Chicago
$93 Roundtrip, just found
$93
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Oct 20 from Denver to Chicago, returning Wed, Oct 22, priced at $93 just found
Frontier Airlines
Sat, Aug 30 - Sat, Sep 6
DEN
Denver
ORD
Chicago
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Denver to Chicago, returning Sat, Sep 6, priced at $102 found 1 hour ago
Frontier Airlines
Thu, Oct 2 - Mon, Oct 6
DEN
Denver
ORD
Chicago
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 2 from Denver to Chicago, returning Mon, Oct 6, priced at $106 just found
Frontier Airlines
Mon, Sep 8 - Mon, Sep 15
DEN
Denver
MDW
Chicago
$107 Roundtrip, found 19 hours ago
$107
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Sep 8 from Denver to Chicago, returning Mon, Sep 15, priced at $107 found 19 hours ago
Southwest Airlines
Tue, Sep 16 - Thu, Sep 18
DEN
Denver
MDW
Chicago
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Denver to Chicago, returning Thu, Sep 18, priced at $135 found 4 days ago
American Airlines
Tue, Sep 30 - Wed, Oct 1
DEN
Denver
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 30 from Denver to Chicago, returning Wed, Oct 1, priced at $137 just found
United
Tue, Sep 30 - Wed, Oct 1
DEN
Denver
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Tue, Sep 30 from Denver to Chicago, returning Wed, Oct 1, priced at $137 just found
Delta
Sat, Oct 25 - Tue, Oct 28
DEN
Denver
ORD
Chicago
$196 Roundtrip, found 3 hours ago
$196
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Oct 25 from Denver to Chicago, returning Tue, Oct 28, priced at $196 found 3 hours ago

Find the cheapest month to fly from Denver (DEN) to Chicago (CHI)

September is typically the cheapest month to fly

From $48 - $166 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $111
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $111
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $197
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $197
Flights from Denver (DEN) to Chicago (ORD)
Origin airport
Denver Intl.
Destination airport
O'Hare Intl.
Roundtrip price
$80
Distance
886 mi

Denver to Chicago Flights

The cheapest times to fly from Denver to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Denver to Chicago are during the month of September. You can find some of the cheapest flights from Denver to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Denver to Chicago

Sunday is one of the best days to book for cheap flights from Denver to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Denver to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Denver to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $45 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Denver to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Denver to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much is a flight from DIA airport to Chicago, IL (CHI-All Airports)?
If you're planning on traveling between DEN and Chicago, IL (CHI-All Airports), round-trip journeys start from $80. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Denver Intl. Airport (DEN) to Chicago, IL (CHI-All Airports)?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from Denver Airport to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for DEN to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Denver Airport to Chicago, IL (CHI-All Airports)?
That new movie you've been desperate to see will just have to wait — the flight distance between DEN and Chicago, IL (CHI-All Airports) is only 839 mi. The captain will be telling you to put your seat upright for landing before you know it.
Which airlines fly direct from DIA airport to Chicago, IL (CHI-All Airports)?
Traveling from Denver Airport to Chicago, IL (CHI-All Airports) is easy when you have a good range of airlines to select from. These are some of the best:

  • Southwest Airlines - (WN) with 434 monthly flights
  • United Airlines - (UA) with 269 monthly flights
  • American Airlines - (AA) with 91 monthly flights
  • Frontier Airlines - (F9) with 47 monthly flights

Are Denver Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Denver Intl. Airport (DEN) to Chicago, IL (CHI-All Airports) last minute could be your ticket to a fantastic deal. However, you might miss out on a flight altogether! If you'd rather err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back often as deals are updated all the time on Expedia.

Explore a world of travel with Expedia

*Available to One Key members.