Cheap Flight Tickets from Denver (DEN) to Chicago (MDW), Starting at $206

Good to Know: Cheapest and Fastest DEN - MDW Flights

Useful information for finding best airline tickets from Denver International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$209

WN Southwest Airlines • 1 stop • 10h 5m

Nov 12 – Nov 12

The cheapest round trip flight from Denver to Chicago (DEN-MDW-DEN) is currently $209

🔍 Search Flights

Cheapest Direct Flight

$206

WN Southwest Airlines • nonstop • 3h 40m

Nov 12

The cheapest nonstop flight from Denver to Chicago (DEN-MDW) is currently $206

🔍 Search Flights

Fastest Flight

3h 35m

The fastest nonstop flight from Denver to Chicago (DEN-MDW) takes 3h 35m

Top Airlines Flying from Denver to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Sun Country Airlines (SY)

Sun Country Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Denver (DEN) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Denver to Chicago. Ideal for travelers with confirmed return itineraries.

Nov 12 - Nov 12, Economy
WN
Denver → Chicago
10h 5m
8:40 AM - 3:45 PM • 1 stop
WN
Denver → Chicago
4h 10m
9:25 PM - 11:15 PM • nonstop
$209
Southwest Airlines
Nov 12 - Nov 12, Economy
WN
Denver → Chicago
3h 35m
2:45 PM - 6:00 PM • nonstop
WN
Denver → Chicago
17h
10:05 PM - 7:25 AM • 1 stop
$209
Southwest Airlines
Nov 12 - Nov 12, Economy
WN
Denver → Chicago
15h 10m
5:35 AM - 3:45 PM • 1 stop
WN
Denver → Chicago
4h 10m
9:25 PM - 11:15 PM • nonstop
$209
Southwest Airlines
Nov 12 - Nov 12, Economy
WN
Denver → Chicago
8h 20m
8:10 AM - 2:10 PM • 1 stop
WN
Denver → Chicago
9h 5m
6:30 PM - 11:15 PM • 1 stop
$212
Southwest Airlines
Nov 12 - Nov 12, Economy
DL
Denver → Chicago
9h 1m
6:10 AM - 12:51 PM • 1 stop
UA
Denver → Chicago
4h 13m
4:20 PM - 6:13 PM • nonstop
$868
Delta Airlines
Nov 12 - Nov 12, Economy
DL
Denver → Chicago
7h
6:30 AM - 11:50 AM • 1 stop
UA
Denver → Chicago
4h 13m
2:30 PM - 4:23 PM • nonstop
$868
Delta Airlines

Fly from Denver to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Denver to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Denver to Chicago Flights

What are the airports in Denver?
DEN
What’s the most popular airline flying from DEN to MDW?
The most popular airline flying from Denver to Chicago are
Can I fly from DEN to MDW non-stop?
Yes, you can fly DEN to MDW non-stop on
Which airlines fly nonstop between Denver and Chicago?
The non-stop flights between Denver and Chicago are .
What’s the earliest departure time from DEN to MDW Airport?
The earliest flight leaves DEN at 5:35 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Denver to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from DEN to MDW?
Read the fare rules of the Denver to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Denver and Chicago?
operate flights between Denver and Chicago
How long does a flight from Denver to Chicago take?
It takes approximately 2 hour to fly non-stop from DEN to MDW, which is 895.33 miles by air.
Which airlines provide the cheapest flights from Denver (DEN) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from DEN were found on WN : USD 212
Do I need a passport to fly between DEN and MDW?
No
What’s the latest departure time from DEN to MDW ?
The last flight leaves DEN at 6:05 pm

Hotels in Chicago (MDW)

5 hotels near Chicago Midway International — compare rates from top booking sites.

View All Hotels →
4.0-star hotel 4-star hotel

Doubletree By Hilton Hotel Chicago Alsip

📍 5000 West 127th Street, Alsip, Illinois 60803

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

Hyatt Regency McCormick Place

📍 2233 S Martin Luther King Dr, Chicago, Illinois 60616

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

MileNorth Hotel

📍 166 E Superior Street, Chicago, Illinois 60611

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

Sheraton Grand Chicago

📍 301 E North Water St, Chicago, Illinois 60611

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

The Westin Michigan Avenue Chicago

📍 909 North Michigan Ave, Chicago, Illinois 60611

Compare booking sites Search Deals →
Hotel Deals in Chicago (IL)
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
Red Roof Inn

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

6.6/10
★★☆☆☆ Hotel 132.0 rooms
✓ Free WiFi

📍 22 West Algonquin Road, Chicago (IL)

Experience an abundance of unparalleled facilities and features at Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts. Maintain seamless communication using the complimentary Wi-Fi at hotel.For visit…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$56/night
View Deal
Baymont by Wyndham Glenview
Wyndham Hotels & Resorts

Baymont by Wyndham Glenview

8.0/10
★★★☆☆ Hotel 95.0 rooms
✓ Free WiFi ✓ Breakfast

📍 1625 Milwaukee Ave, Chicago (IL), Illinois

At Baymont by Wyndham Glenview, exceptional service and top-notch amenities create a memorable experience for guests.Complimentary internet access is available in the hotel to ensure you stay connect…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$92/night
View Deal
Radisson Hotel Schaumburg
Choice Hotels

Radisson Hotel Schaumburg

6.9/10
★★★☆☆ Hotel 127.0 rooms
✓ Free WiFi ✓ Breakfast

📍 1550 N. Roselle Rd, Chicago (IL), Illinois

Radisson Hotel Schaumburg provides flawless service and all the necessary facilities for visitors. Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. W…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$95/night
View Deal
Best Western at O'Hare
Best Western International

Best Western at O'Hare

7.9/10
Hotel 141.0 rooms
✓ Free WiFi ✓ Breakfast

📍 10300 W Higgins Road, Chicago (IL), Illinois

At Best Western at OHare, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the hotel to ensure you stay connected du…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$115/night
View Deal
Chicago South Loop
No chain

Chicago South Loop

7.7/10
★★★☆☆ Hotel 232.0 rooms
✓ Free WiFi

📍 11 W 26th Street, Chicago (IL), Illinois

Chicago South Loop offers top-notch services and amenities, ensuring guests experience utmost comfort.Maintain seamless communication using the complimentary Wi-Fi at hotel. For visitors traveling by…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$140/night
View Deal
Freehand Chicago
No chain

Freehand Chicago

8.0/10
★★★★☆ Hotel 215.0 rooms
✓ Free WiFi

📍 19 East Ohio Street, Chicago (IL), Illinois

At Freehand Chicago, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the hotel to ensure you stay connected during …

Check-in 03:00 PM  ·  Check-out 12:00 PM

$142/night
View Deal
Silversmith Hotel Chicago Downtown
No chain

Silversmith Hotel Chicago Downtown

8.7/10
★★★★☆ Hotel 144.0 rooms
✓ Free WiFi

📍 10 South Wabash Avenue, Chicago (IL), Illinois

Great care is taken to ensure guests experience comfort through top-notch services and amenities. Remain linked during your visit by utilizing the complimentary internet access available.Parking is a…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$142/night
View Deal
Travelodge by Wyndham Downtown Chicago
Wyndham Hotels & Resorts

Travelodge by Wyndham Downtown Chicago

7.6/10
★★☆☆☆ Hotel 233.0 rooms
✓ Free WiFi

📍 65 E. Harrison, Chicago (IL), Illinois

Travelodge by Wyndham Downtown Chicago offers top-notch services and amenities, ensuring guests experience utmost comfort.Share your photos and respond to emails at your convenience, thanks to the fr…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$183/night
View Deal
Millennium Hotel Knickerbocker Chicago
Millennium & Copthorne Hotels

Millennium Hotel Knickerbocker Chicago

8.2/10
★★★★☆ Hotel 306.0 rooms
✓ Free WiFi ✓ Breakfast

📍 163 East Walton Place, Chicago (IL), Illinois

Experience an abundance of unparalleled facilities and features at Millennium Knickerbocker Chicago. Maintain seamless communication using the complimentary Wi-Fi at hotel.Discovering Chicago (IL) be…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$192/night
View Deal

Denver (DEN) to Chicago (MDW): Airport Information

Origin Airport Denver International , Denver, US
Destination Airport Chicago Midway International , Chicago, US
Distance 895 miles

More Flight Options for Denver (DEN) and Chicago (MDW)

Why Fareleaders for DEN to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Denver to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on DEN to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Denver to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Denver (DEN) to Chicago (MDW)
Terms and Conditions*