DEN - CHI

$106 Find Cheap Flights from Denver to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$162
Typical prices: $196-$353
Frontier
Tue 11/6Fri 11/9
DEN - ORD • Non-stop
Cheapest one-way
$106
Typical prices: $120-$243
Frontier
Tue 10/16
DEN - ORD • 1 stop
Advice from real travelers
Frontier Economy Bundle adds a carry-on and seat selection; Premium Bundle adds legroom.
United Economy Plus adds up to 6 inches more legroom; American Main Cabin Extra adds perks.
Expert advice
+1
Expert advice
+1
Nonstop flights
You can fly direct with United Airlines, American Airlines and others. Average duration is 2h 36m.
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 3% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $215 (round-trip)
Shortest trip • 5h 57m (one-way)
Insights
Insights
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Denver to Chicago (DEN-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Denver to Chicago

Fri, Nov 6 - Mon, Nov 9
Frontier Logo
8:55 pm - 12:21 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 26mnonstop
Frontier Logo
6:30 am - 8:26 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 56mnonstop
$162Frontier
Fri, Nov 6 - Mon, Nov 9
Frontier Logo
8:55 pm - 12:21 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 26mnonstop
Frontier Logo
6:30 am - 8:26 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 56mnonstop
$162Frontier
Wed, Nov 4 - Mon, Nov 9
Multiple Airlines Logo
9:10 pm - 6:05 pmDEN  Denver Intl-ORD Chicago O'Hare Intl
19h 55m1 stop Minneapolis St Paul
Multiple Airlines Logo
6:30 am - 8:26 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 56mnonstop
$183Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
9:10 pm - 10:41 amDEN  Denver Intl-ORD Chicago O'Hare Intl
12h 31m1 stop Minneapolis St Paul
Multiple Airlines Logo
6:30 am - 8:26 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 56mnonstop
$183Multiple Airlines
Tue, Sep 29 - Tue, Sep 29
United Airlines Logo
6:00 am - 9:43 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 43mnonstop
United Airlines Logo
7:50 pm - 9:44 pmORD  Chicago O'Hare Intl-DEN Denver Intl
2h 54mnonstop
$229United Airlines
Tue, Dec 22 - Wed, Dec 30
United Airlines Logo
5:56 pm - 9:29 pmDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 33mnonstop
United Airlines Logo
9:20 pm - 11:20 pmORD  Chicago O'Hare Intl-DEN Denver Intl
3h 00mnonstop
$229United Airlines
Sat, Oct 3 - Tue, Oct 6
American Airlines Logo
8:18 am - 11:59 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 41mnonstop
American Airlines Logo
9:45 am - 11:37 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 52mnonstop
$229American Airlines
Thu, Dec 24 - Tue, Dec 29
American Airlines Logo
7:21 am - 11:05 amDEN  Denver Intl-ORD Chicago O'Hare Intl
2h 44mnonstop
American Airlines Logo
10:35 pm - 12:32 amORD  Chicago O'Hare Intl-DEN Denver Intl
2h 57mnonstop
$229American Airlines
Wed, Oct 7 - Wed, Oct 14
Southwest Logo
7:50 pm - 11:15 pmDEN  Denver Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
7:40 am - 9:15 amMDW  Chicago Midway-DEN Denver Intl
2h 35mnonstop
$229Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
8:55 pm - 12:15 amDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
9:20 pm - 11:05 pmMDW  Chicago Midway-DEN Denver Intl
2h 45mnonstop
$229Southwest
Booking Insights

Price, demand and travel trends for Denver to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Denver to Chicago with more confidence.

How much is a round-trip flight from Denver to Chicago?

Round-trip flights from Denver to Chicago start at $162. Prices are below average for this route right now, with typical round-trip fares ranging from $196 to $353. The lowest price found in the past 5 days was $162 on Frontier.

What is the cheapest Denver to Chicago flight route?

There's little price difference between Denver to Chicago routes. They average around $268 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Denver to Chicago?

Friday is the cheapest day of the week to fly from Denver to Chicago, it is 4% cheaper than the average day. Sunday is the most expensive day with flight prices 24% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Denver to Chicago?

  • January is the cheapest month to fly from Denver to Chicago at $202 round-trip.
  • June ($310) and July ($306) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 53% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Denver to Chicago the cheapest?

Flights from Denver to Chicago are cheapest 12 weeks before departure. Booking in this window typically costs about 38% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Denver to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines and DEN

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Key details for Denver to Chicago flights

Low season

February

Cheapest flight

$106
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Denver to Chicago O'Hare Intl Airport

When to book flights from Denver to Chicago

Are your dates flexible? Find out the best times to travel from Denver to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Flights from Denver to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Denver to Chicago 
JoanneFlew with United Airlines-Jun 2026
The runway to gate took a bit of time. So if you have a short layover pay for a seat up front .
AdamFlew with Southwest-Oct 2024
Arriving T5 at ORD on Southwest is often a LONG walk, with no moving walkways going out, to baggage claim / pickup.
BrianFlew with United Airlines-Jan 2024
Big airport. Make sure you have enough time between flights for rest, eating, etc…

Your Denver to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • What are some good hotel options near Chicago Midway International Airport?

    The Hyatt Place is a modern hotel that is a 25-minute drive from downtown Chicago and a 6-minute drive from Chicago Midway International Airport. The Holiday Inn Express & Suites is a 4-star choice that is a 5-minute drive from the Ford City Mall and a 3-minute drive from the airport.

  • Is there anywhere to shower at O’Hare International Airport?

    If you would like to freshen up after your flight has landed, there are several places where you can shower in O’Hare International Airport. Both the American Airlines Admirals Club and United Club lounges have private showers that can be used by anyone with an access pass. The Hilton Athletic Club also has showers that can be used by guests.

  • What is there to do at Denver International Airport?

    If you enjoy art, make sure to look at the various art exhibits that are located inside of Denver International Airport, including several outdoor landscapes that contain small statues. If you like video games, head to one of the gaming booths that are located throughout all the terminals and can be rented for a small fee.

  • What shopping options are there at Denver International Airport?

    Because of its diverse selection of shops, Denver International Airport is a convenient place to purchase souvenirs and gifts. Bearfruit Jewelry is located near the A Gates and sells a variety of accessories, while Route 70 Clothing is located near the B Gates and offers apparel items.

  • Is there public transportation from downtown Denver to Denver Airport?

    Yes, Denver has a commuter train that takes you directly from the city center to the Denver International Airport (DEN). This is the most convenient public transit round, avoiding worrying about traffic and parking before your flight to Chicago. It takes about 30-40 minutes on the A-Line. You can expect it to cost around $10.50 per day.

  • What accessibility services are available for passengers flying out of Denver Airport?

    If you have reduced mobility and require assistance to catch your flight out of Denver International Airport (DEN), you can book the airport’s meet and assist service. This includes help from the terminal entrance, through TSA security, to your gate. Make sure you reserve it at least 48 hours before your departure time.

  • From which airport is it more convenient to get to Millennium Park?

    Both Chicago O’Hare International Airport (ORD) and Chicago Midway Airport (MDW) have direct subway routes to the iconic Millennium Park and The Bean. Nonetheless, the trip by train from Chicago Midway is shorter. From this airport, closer to the city center, you can be walking around Millennium Park in about 35 minutes if you take the Orange Line.

  • Where can I drop off my car rental in Chicago O’Hare (ORD)?

    For those dropping off their Chicago O’Hare International Airport (ORD) rental car, the different agencies available at the airport are located at the Multi-Modal Facility outside the airport area. However, there are Airport Transit System shuttles that connect the MMF with all the different Chicago O’Hare terminals.

  • Which airlines offer extra legroom and free seat selection on Denver to Chicago flights?

    Among airlines operating Denver to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • Frontier: offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Denver to Chicago?

    4 airlines operate flights between Denver and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest
    • Frontier

  • Which airports can I use when flying from Denver to Chicago?

    Flights from Denver to Chicago usually depart from Denver Intl (DEN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airlines include bags at no extra cost on Denver to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • Frontier: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Denver to Chicago?

    Four cabin classes are available on flights from Denver to Chicago:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How much can I save by taking a layover when flying from Denver to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $215 round-trip via Dallas/Fort Worth (DFW), compared to $266 for nonstop.

  • What is the standard checked-bag allowance on flights from Denver to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Denver to Chicago pass through?

    One-stop flights from Denver to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 36% of one-stop connections
    • Minneapolis St Paul (MSP) - 28% of one-stop connections
    • Dallas/Fort Worth (DFW) - 17% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 14% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Denver to Chicago?

    Yes. Being flexible with your travel dates can save you up to 23% on the Denver to Chicago route. Friday is the cheapest departure day at $254 round-trip on average, while Sunday is the most expensive at $328, a difference of $74. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Denver to Chicago spread across the day?

    Morning is the busiest departure period on Denver to Chicago flights, with 43% of flights leaving in that window. Afternoon departures account for 31%, evening flights for 26%, and night flights for 0%.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • What are the earliest and latest flights from Denver to Chicago?

    These are the earliest and latest flight times available from Denver to Chicago:

    • Earliest: departs at 5:00 am and lands at 7:36 am
    • Latest: departs at 9:26 pm and lands at 12:02 am.

    The flight takes about 2h 36m.

  • How expensive are last-minute Denver to Chicago flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 31% above the route average of $264. Book 12 weeks before departure for the lowest fares.

  • How long is a flight from Denver to Chicago?

    A nonstop flight from Denver to Chicago takes 2h 36m, covering 899 miles.

  • Do I need a passport to fly from Denver to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • How are flight prices from Denver to Chicago looking right now?

    One-way fares from Denver to Chicago are currently lower than usual. Average one-way flight prices are about $112, which is 35% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Denver to Chicago?

    Flying via Chicago O'Hare Intl (ORD) gives the shortest average 1-stop total travel time at 5h 57m, compared with 6h 03m via Detroit Metropolitan Wayne County (DTW) and 6h 07m via Minneapolis St Paul (MSP).

  • What is the time difference between Denver and Chicago?

    Chicago is 1 hour ahead of Denver (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    · Routes Car & Truck Rentals
    · Europcar
    · Hertz
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    · Alamo
    · Enterprise Rent-A-Car
    · Budget
    · Avis
    · National

  • How much should I expect to pay for a Denver to Chicago flight?

    Round-trip flights from Denver to Chicago range from $196 to $353, with an average of $264 over the past 12 months. Anything below $196 counts as a good deal.

  • Which airlines offer Wi-Fi on Denver to Chicago flights?

    Two airlines offer in-flight Wi-Fi on Denver to Chicago flights:

    • • American Airlines
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Denver to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Friday departure instead of Sunday. On this route, Friday flights average $254 - about $74 less than Sunday (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 38% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Denver to Chicago trip for January. Fares historically average $202 round-trip in that month - typically $108 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Dallas/Fort Worth Airport (DFW) can be cheaper than flying direct. The cheapest layover option averages $215 round-trip on this route - about $51 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel
  • When booking flights from Denver to Chicago, there are two primary airports that you can land at. If you will be staying in the northern region of the city, consider flying into O'Hare International Airport. If you will be staying in the southern region of the city, it is more convenient to fly into Chicago Midway International Airport.
  • An easy way to make your travel experience as quick and carefree as possible is to book a direct flight from Denver to Chicago. Spirit and Frontier Airlines offer a variety of tickets at budget-friendly prices, while United Airlines has an option to upgrade to a more comfortable seat for a small fee.
  • For those who are traveling for business, stop by the business center that is located near the B Gates of Denver International Airport. Equipped with high-speed Internet, desks, and fax and copying services, this center is a convenient place to work on your to-do list before boarding your flight.
  • If you are hungry after your flight has landed, check out some of the diverse dining options in O’Hare International Airport. Berghoff Cafe is a casual choice that is located in Terminal 1 and serves a variety of sandwiches, while Macaroni Grill is in Terminal 3 and has Italian-inspired cuisine.
  • To unwind before a long day of traveling, pay a visit to one of the A Massage locations near Gates A and B of Denver International Airport. These salons offer both table and chair massages, allowing travelers to melt their stress away before officially embarking on their travels.
  • If you’re flying into Chicago for a long layover or just a short trip to the city, Chicago O’Hare International Airport (ORD) has an on-site hotel. You’ll find the Hilton Chicago O’Hare Airport Hotel right across from Terminals 1, 2, and 3 and connected with underground walkways to the International Halls.
  • Upon your arrival at Chicago Midway Airport (MDW), you can check out some of the art on display. There are various sculptures, murals, and paintings throughout the concourses. For instance, there’s the display of the Dauntless Diver airplane at the exit of Concourse A.
  • Hop on the Blue Line of the subway to get from the Chicago O’Hare International Airport (ORD) to Downtown Chicago in just around 50 minutes. You can expect it to cost about $2-5.
  • Although it is possible to find direct flights from Denver International Airport (DEN) to Chicago, sometimes it’s more convenient or affordable to book a route that has a layover in between. In this case, you can fly to Chicago O’Hare International Airport (ORD) with Delta Airlines, stopping in Minneapolis-St Paul (MSP) on the way.
  • There are four different pet relief areas at Denver International Airport (DEN). Bring your furry friends here to stretch their legs and relieve themselves before your flight to Chicago. You’ll find one on Level 2 of each of the center cores of Concourses A, B, and C, and the northwest side of Level 2 in the Jeppesen Terminal.

Prefer to fly direct from Denver to Chicago?

 
Find which airlines fly direct from Denver Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Denver Intl to Chicago

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Chicago to Denver Intl

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

More options for your flight from Denver to Chicago

Complete your trip to Chicago with a hotel stay or car rental