Cheap Flights from Denver to Chicago (DEN to ORD)

Discover more affordable routes and cheaper dates from Denver to Chicago (DEN to ORD) within a date range.

⭐ Search by country or region to discover more affordable routes, like Netherlands → Italy or Europe → South East Asia.

Results Quantity

Cabin Bags

Checked Bags

Max Budget

US$

Max Duration

Hours

Max Layover

Hours

Departure Time

Connections

Select Airlines

Loading…

US$31

9:08pm - 12:44am
Mon Mar 17th 2025

2h 36m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 Frontier Airlines · F9 3172 Depart at 9:08pm from Denver (DEN) Fly for 2h 36m Arrive at 12:44am in Chicago (ORD)

Book Flight
US$103

8:50pm - 12:23am
Sun Mar 16th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 Frontier Airlines · F9 3172 Depart at 8:50pm from Denver (DEN) Fly for 2h 33m Arrive at 12:23am in Chicago (ORD)

Book Flight
US$121

8:55pm - 12:23am
Sat Mar 15th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 377 Depart at 8:55pm from Denver (DEN) Fly for 2h 28m Arrive at 12:23am in Chicago (ORD)

Book Flight
US$124

9:48am - 1:20pm
Sat Mar 15th 2025

2h 32m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 Frontier Airlines · F9 3174 Depart at 9:48am from Denver (DEN) Fly for 2h 32m Arrive at 1:20pm in Chicago (ORD)

Book Flight
US$143

9:08pm - 12:44am
Fri Mar 14th 2025

2h 36m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 Frontier Airlines · F9 3172 Depart at 9:08pm from Denver (DEN) Fly for 2h 36m Arrive at 12:44am in Chicago (ORD)

Book Flight
US$144

5:30am - 2:16pm
Mon Mar 17th 2025

7h 46m
Denver (DEN) → Chicago (ORD)

1 Stop

Mon Mar 17th 2025 Frontier Airlines · F9 4464 Depart at 5:30am from Denver (DEN) Fly for 2h 8m Arrive at 8:38am in Dallas (DFW)

Layover in Dallas for 3h 4m

Mon Mar 17th 2025 Frontier Airlines · F9 3242 Depart at 11:42am from Dallas (DFW) Fly for 2h 34m Arrive at 2:16pm in Chicago (ORD)

Book Flight
US$150

5:11pm - 5:04am
Mon Mar 17th 2025

10h 53m
Denver (DEN) → Chicago (ORD)

1 Stop

Mon Mar 17th 2025 Frontier Airlines · F9 777 Depart at 5:11pm from Denver (DEN) Fly for 2h 12m Arrive at 6:23pm in Las Vegas (LAS)

Layover in Las Vegas for 4h 57m

Mon Mar 17th 2025 Frontier Airlines · F9 2146 Depart at 11:20pm from Las Vegas (LAS) Fly for 3h 44m Arrive at 5:04am in Chicago (ORD)

Book Flight
US$150

8:23am - 9:19pm
Mon Mar 17th 2025

11h 56m
Denver (DEN) → Chicago (ORD)

1 Stop

Mon Mar 17th 2025 Frontier Airlines · F9 3981 Depart at 8:23am from Denver (DEN) Fly for 1h 42m Arrive at 10:05am in Salt Lake City (SLC)

Layover in Salt Lake City for 7h 0m

Mon Mar 17th 2025 Frontier Airlines · F9 2028 Depart at 5:05pm from Salt Lake City (SLC) Fly for 3h 14m Arrive at 9:19pm in Chicago (ORD)

Book Flight
US$150

6:17am - 9:19pm
Mon Mar 17th 2025

14h 2m
Denver (DEN) → Chicago (ORD)

1 Stop

Mon Mar 17th 2025 Frontier Airlines · F9 3861 Depart at 6:17am from Denver (DEN) Fly for 1h 41m Arrive at 7:58am in Salt Lake City (SLC)

Layover in Salt Lake City for 9h 7m

Mon Mar 17th 2025 Frontier Airlines · F9 2028 Depart at 5:05pm from Salt Lake City (SLC) Fly for 3h 14m Arrive at 9:19pm in Chicago (ORD)

Book Flight
US$155

8:55pm - 12:23am
Mon Mar 17th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 377 Depart at 8:55pm from Denver (DEN) Fly for 2h 28m Arrive at 12:23am in Chicago (ORD)

Book Flight
US$155

6:00am - 9:33am
Mon Mar 17th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 532 Depart at 6:00am from Denver (DEN) Fly for 2h 33m Arrive at 9:33am in Chicago (ORD)

Book Flight
US$155

5:55pm - 9:28pm
Mon Mar 17th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 1898 Depart at 5:55pm from Denver (DEN) Fly for 2h 33m Arrive at 9:28pm in Chicago (ORD)

Book Flight
US$161

7:23pm - 10:51pm
Sat Mar 15th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 2258 Depart at 7:23pm from Denver (DEN) Fly for 2h 28m Arrive at 10:51pm in Chicago (ORD)

Book Flight
US$166

6:00am - 9:33am
Sun Mar 16th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 532 Depart at 6:00am from Denver (DEN) Fly for 2h 33m Arrive at 9:33am in Chicago (ORD)

Book Flight
US$166

4:22pm - 7:55pm
Mon Mar 17th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 1495 Depart at 4:22pm from Denver (DEN) Fly for 2h 33m Arrive at 7:55pm in Chicago (ORD)

Book Flight
US$166

8:55pm - 12:23am
Fri Mar 14th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 377 Depart at 8:55pm from Denver (DEN) Fly for 2h 28m Arrive at 12:23am in Chicago (ORD)

Book Flight
US$170

7:46am - 11:19am
Sun Mar 16th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 530 Depart at 7:46am from Denver (DEN) Fly for 2h 33m Arrive at 11:19am in Chicago (ORD)

Book Flight
US$178

5:55pm - 9:28pm
Sat Mar 15th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 1898 Depart at 5:55pm from Denver (DEN) Fly for 2h 33m Arrive at 9:28pm in Chicago (ORD)

Book Flight
US$187

7:39pm - 5:04am
Mon Mar 17th 2025

8h 25m
Denver (DEN) → Chicago (ORD)

1 Stop

Mon Mar 17th 2025 Frontier Airlines · F9 4967 Depart at 7:39pm from Denver (DEN) Fly for 2h 9m Arrive at 8:48pm in Las Vegas (LAS)

Layover in Las Vegas for 2h 32m

Mon Mar 17th 2025 Frontier Airlines · F9 2146 Depart at 11:20pm from Las Vegas (LAS) Fly for 3h 44m Arrive at 5:04am in Chicago (ORD)

Book Flight
US$199

7:17pm - 10:45pm
Fri Mar 14th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 2258 Depart at 7:17pm from Denver (DEN) Fly for 2h 28m Arrive at 10:45pm in Chicago (ORD)

Book Flight
US$199

8:55pm - 12:23am
Sun Mar 16th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 377 Depart at 8:55pm from Denver (DEN) Fly for 2h 28m Arrive at 12:23am in Chicago (ORD)

Book Flight
US$199

4:22pm - 7:55pm
Fri Mar 14th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 1495 Depart at 4:22pm from Denver (DEN) Fly for 2h 33m Arrive at 7:55pm in Chicago (ORD)

Book Flight
US$199

6:00am - 9:33am
Fri Mar 14th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 532 Depart at 6:00am from Denver (DEN) Fly for 2h 33m Arrive at 9:33am in Chicago (ORD)

Book Flight
US$199

7:46am - 11:19am
Fri Mar 14th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 530 Depart at 7:46am from Denver (DEN) Fly for 2h 33m Arrive at 11:19am in Chicago (ORD)

Book Flight
US$199

5:55pm - 9:28pm
Fri Mar 14th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 1898 Depart at 5:55pm from Denver (DEN) Fly for 2h 33m Arrive at 9:28pm in Chicago (ORD)

Book Flight
US$200

3:22pm - 6:55pm
Mon Mar 17th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 1012 Depart at 3:22pm from Denver (DEN) Fly for 2h 33m Arrive at 6:55pm in Chicago (ORD)

Book Flight
US$200

7:46am - 11:19am
Mon Mar 17th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 530 Depart at 7:46am from Denver (DEN) Fly for 2h 33m Arrive at 11:19am in Chicago (ORD)

Book Flight
US$215

7:46am - 11:19am
Sat Mar 15th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 530 Depart at 7:46am from Denver (DEN) Fly for 2h 33m Arrive at 11:19am in Chicago (ORD)

Book Flight
US$215

6:00am - 9:33am
Sat Mar 15th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 532 Depart at 6:00am from Denver (DEN) Fly for 2h 33m Arrive at 9:33am in Chicago (ORD)

Book Flight
US$215

3:22pm - 6:55pm
Sat Mar 15th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 1012 Depart at 3:22pm from Denver (DEN) Fly for 2h 33m Arrive at 6:55pm in Chicago (ORD)

Book Flight
US$215

4:22pm - 7:55pm
Sat Mar 15th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 1495 Depart at 4:22pm from Denver (DEN) Fly for 2h 33m Arrive at 7:55pm in Chicago (ORD)

Book Flight
US$242

1:25pm - 4:51pm
Fri Mar 14th 2025

2h 26m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 617 Depart at 1:25pm from Denver (DEN) Fly for 2h 26m Arrive at 4:51pm in Chicago (ORD)

Book Flight
US$242

3:22pm - 6:55pm
Fri Mar 14th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 1012 Depart at 3:22pm from Denver (DEN) Fly for 2h 33m Arrive at 6:55pm in Chicago (ORD)

Book Flight
US$242

7:17pm - 10:45pm
Sun Mar 16th 2025

2h 28m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 2258 Depart at 7:17pm from Denver (DEN) Fly for 2h 28m Arrive at 10:45pm in Chicago (ORD)

Book Flight
US$242

4:22pm - 7:55pm
Sun Mar 16th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 1495 Depart at 4:22pm from Denver (DEN) Fly for 2h 33m Arrive at 7:55pm in Chicago (ORD)

Book Flight
US$242

5:55pm - 9:28pm
Sun Mar 16th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 1898 Depart at 5:55pm from Denver (DEN) Fly for 2h 33m Arrive at 9:28pm in Chicago (ORD)

Book Flight
US$243

1:25pm - 4:51pm
Mon Mar 17th 2025

2h 26m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 617 Depart at 1:25pm from Denver (DEN) Fly for 2h 26m Arrive at 4:51pm in Chicago (ORD)

Book Flight
US$292

3:22pm - 6:55pm
Sun Mar 16th 2025

2h 33m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 1012 Depart at 3:22pm from Denver (DEN) Fly for 2h 33m Arrive at 6:55pm in Chicago (ORD)

Book Flight
US$292

9:40am - 1:14pm
Fri Mar 14th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 2329 Depart at 9:40am from Denver (DEN) Fly for 2h 34m Arrive at 1:14pm in Chicago (ORD)

Book Flight
US$292

11:20am - 2:54pm
Fri Mar 14th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Fri Mar 14th 2025 United Airlines · UA 1727 Depart at 11:20am from Denver (DEN) Fly for 2h 34m Arrive at 2:54pm in Chicago (ORD)

Book Flight
US$293

9:40am - 1:14pm
Mon Mar 17th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 2329 Depart at 9:40am from Denver (DEN) Fly for 2h 34m Arrive at 1:14pm in Chicago (ORD)

Book Flight
US$293

11:20am - 2:54pm
Mon Mar 17th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Mon Mar 17th 2025 United Airlines · UA 1727 Depart at 11:20am from Denver (DEN) Fly for 2h 34m Arrive at 2:54pm in Chicago (ORD)

Book Flight
US$300

1:25pm - 4:51pm
Sat Mar 15th 2025

2h 26m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 617 Depart at 1:25pm from Denver (DEN) Fly for 2h 26m Arrive at 4:51pm in Chicago (ORD)

Book Flight
US$300

9:40am - 1:14pm
Sat Mar 15th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 2329 Depart at 9:40am from Denver (DEN) Fly for 2h 34m Arrive at 1:14pm in Chicago (ORD)

Book Flight
US$329

9:40am - 1:14pm
Sun Mar 16th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 2329 Depart at 9:40am from Denver (DEN) Fly for 2h 34m Arrive at 1:14pm in Chicago (ORD)

Book Flight
US$342

11:20am - 2:54pm
Sat Mar 15th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Sat Mar 15th 2025 United Airlines · UA 1727 Depart at 11:20am from Denver (DEN) Fly for 2h 34m Arrive at 2:54pm in Chicago (ORD)

Book Flight
US$383

11:15am - 2:49pm
Sun Mar 16th 2025

2h 34m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 1727 Depart at 11:15am from Denver (DEN) Fly for 2h 34m Arrive at 2:49pm in Chicago (ORD)

Book Flight
US$478

1:25pm - 4:51pm
Sun Mar 16th 2025

2h 26m
Denver (DEN) → Chicago (ORD)

Direct

Sun Mar 16th 2025 United Airlines · UA 617 Depart at 1:25pm from Denver (DEN) Fly for 2h 26m Arrive at 4:51pm in Chicago (ORD)

Book Flight

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality. It's designed for remote workers, backpackers, and people living abroad.

Read Sonaa's 7 Amazing Skyscanner Alternatives for Booking Travel

ANDY TRAVELS

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Read Josh's Ultimate Guide To Find Cheap One Way Flights

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Read Wesley's My Best Cheap Flight Hacks (Why Pay More?)

Cheap Flights from Denver to Chicago (DEN to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

ANDY TRAVELS

Travel With Bender

Wesley Mergard

Latest Cheap Flight Searches

FlightList Blog

Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights

Why I Built FlightList & Solved My Own Problem

About FlightList