Flights from Denver (DEN) to Chicago (MDW)

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Cheapest Flights from Denver (DEN) to Chicago (MDW)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

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Denver to Chicago Flight Information

Find the Cheapest Flights from Denver (DEN) to Chicago (MDW)

Work hard, travel harder! Wotif brings you the cheapest Denver to Chicago flights, making it possible to have a five star holiday without that five star price tag. Browse and compare our top DEN to MDW routes and airport options. So, go ahead and treat yourself, your sweetheart, or the kids to an unforgettable holiday this year.

Denver to Chicago Information

Traveling From
Denver Intl.
Origin Airport
Denver
Origin Airport IATA Code
DEN
Traveling To
Midway Intl.
Destination Airport
Chicago
Destination Airport IATA Code
MDW
Number of Airlines Serving
2
Average Flight Time
4 hours 44 mins
Direct Flight Time
4 hours 20 mins
Flight Price
NZ$905
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time zone:
America/Chicago
Address:
8500 Pena Boulevard
Denver CO, 80249-6340
United States
IATA code:
DEN
Longitude:
-104.673098
Latitude:
39.851382
Time zone:
America/Denver

Denver to Chicago Flight Deals from NZ$905

Considering a quick trip to Chicago, but not sure which is the best route for you? Well, you’re in luck! Wotif has done the hard work, so all you need to do is check out these flights from DEN to MDW. With heaps of cheap fares from Denver, we guarantee you’ll be arriving to your holiday destination in style without emptying your bank account in the process.

It’s easy to book flights to Chicago from Denver  

For a huge choice of flights, simply enter your travel dates and hit search and we’ll hunt out fantastic deals on one-way, return and multi-city airfares to Chicago from Denver from 10 different airlines. If you click the ‘direct flights’ box, you see flights that’ll get you to Chicago in just 4 hour(s) and 20 mins, too.   

Snap up great deals on flights to Chicago from Denver 

Choose from 10 flights a day on average, with prices starting at NZ$905 and rising to NZ$1,212 depending on the cabin class, travel dates, and airline carrier. And if you’re up for a last-minute getaway, you can get great deals on flights from Denver to Chicago today!  

Find cheap airfares to Chicago from Denver 

Here are our insider tips for bagging a flight bargain: 

  • Look for midweek flights and late night, early morning arrival and departure times
  • Check out other airports near Denver and Chicago
  • Avoid peak season (prices tend to be lower in July)
  • Be flexible with your travel dates and you can usually get cheaper options  

Reasons to book your flights to Chicago from Denver with Wotif

Wotif is a super-easy way to find the best flight for you to Chicago. Get more bang for your buck on flight and hotel or car rental combos and download the free Wotif app to tap into exclusive deals. Book now with Wotif and have a great flight!

 

Great places to stay after flight from Denver to Chicago

Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,004 reviews)
"Staff was friendly and accommodating, pool was clean and a great ammenity."

Reviewed on 25 Jun. 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,179 reviews)
"The front desk was very nice and helpful. Unfortunately, it was very hot in the hotel, so it wasn’t quite the refuge we were hoping for. It took a while for our air conditioner to cool the room. But when you stepped out into the hallway, it was like being outside. And with the Parking being across ..."

Reviewed on 27 Jun. 2025

Crowne Plaza Chicago West Loop by IHG
Hyatt House Chicago West Loop
Hyatt House Chicago West Loop
3.5 out of 5
105 N MAY STREET, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
8.8/10 Excellent! (1,005 reviews)
"Our stay at this hotel was awesome their customer service was and the rooms were just as described in the booking. I will definitely be using Hyatt Chicago West/Loop again."

Reviewed on 23 Jun. 2025

Hyatt House Chicago West Loop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.