Cheap flights from Denver to Chicago from $105
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Denver to Chicago departing on 11/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Fri 10/23
8:55 pm-12:24 am
Nonstop2h 29m
Chicago O'Hare Intl
Mon 10/26
7:44 pm-8:22 am
1 stop13h 38m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Sat 11/21
9:26 pm-12:53 am
Nonstop2h 27m
Chicago O'Hare Intl
Mon 11/23
6:40 am-8:36 am
Nonstop2h 56m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Wed 12/16
9:26 pm-12:54 am
Nonstop2h 28m
Chicago O'Hare Intl
Mon 12/21
10:45 am-5:07 pm
1 stop7h 22m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Tue 12/22
7:09 pm-10:42 pm
Nonstop2h 33m
Chicago O'Hare Intl
Tue 1/5
2:24 pm-4:17 pm
Nonstop2h 53m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Thu 12/17
3:25 pm-7:05 pm
Nonstop2h 40m
Chicago O'Hare Intl
Tue 12/22
9:20 pm-11:20 pm
Nonstop3h 00m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Thu 11/12
12:24 pm-4:00 pm
Nonstop2h 36m
Chicago O'Hare Intl
Mon 11/16
6:40 am-8:40 am
Nonstop3h 00m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Wed 11/11
6:50 am-10:30 am
Nonstop2h 40m
Chicago O'Hare Intl
Wed 11/11
3:23 pm-5:20 pm
Nonstop2h 57m
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 12/21
8:55 pm-12:10 am
Nonstop2h 15m
Chicago Midway
Thu 12/24
8:55 pm-10:35 pm
Nonstop2h 40m
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 11/7
6:35 am-9:55 am
Nonstop2h 20m
Chicago Midway
Tue 11/10
8:55 pm-10:40 pm
Nonstop2h 45m
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Tue 12/29
3:48 pm-7:22 pm
Nonstop2h 34m
Chicago O'Hare Intl
Fri 1/1
11:45 am-4:42 pm
1 stop5h 57m
See travel insights to Chicago from
How to get the cheapest flight ticket from Denver to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Denver and Chicago?
Prices are currently low for flights on this route.
Typical prices usually range from $201 to $349.The lowest price recently found on this route was $172.
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Denver, with most prices found around $232. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Denver to Chicago during February average around $251.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $338. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Denver to Chicago for around $560.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Denver to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $561.
What is the cheapest Denver Intl to Chicago flight route?
Fly from Denver Intl to Chicago O'Hare Intl for the best Denver Intl - Chicago flight prices
How far in advance should I book a flight from Denver to Chicago?
You are more likely to see cheaper flights to Chicago from Denver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $304 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Denver for as low as $250 on momondo.
What cabin class options are available on Denver to Chicago flights?
There are 4 cabin classes available to choose from on Denver to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Denver to Chicago flights?
No. A direct flight is the cheapest option for a flight between Denver to Chicago.
How have Denver to Chicago flight prices changed over time?
As of October 2026, prices for Denver to Chicago flights are approximately 18% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Denver Intl to Chicago?
Southwest, Delta, and United Airlines are the most popular carriers operating from Denver Intl to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Denver according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Denver to Chicago on average per day?
As of October 2026, there are 60 flights per day flying from Denver to Chicago. The most common time of day flights depart is 11:00AM, with 48% of flights taking off at noon.
How many flights depart from Denver to Chicago on average per week?
The number of flights available between Denver and Chicago is 422 per week as of October 2026. The most frequent departure day is Wed, with 20% of weekly flights leaving on this day.
When to book flights from Denver to Chicago
Cheap Denver to Chicago (DEN to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Denver to Chicago
Frequently asked questions about flying from Denver to Chicago
How far is Denver Intl to Chicago by plane?
There are 917.4 mi between Denver Intl and Chicago. 2h 15m is a normal flight duration for this route.
When did momondo last update prices for flights from Denver Intl Airport to Chicago?
Prices for flights from Denver Intl Airport to Chicago were last updated today.
How many operators does momondo search for flights from Denver Intl Airport to Chicago?
As of October 2026, there are 5 operators available to choose from for flights from Denver Intl Airport to Chicago.
How old do you have to be to fly from Denver Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Denver Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Denver to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Denver to Chicago is Airbus A321neo, representing 18.50% of all bookings. The subsequent popular models are Airbus A321-100/200 at 13.67%, Boeing 737-800 at 11.35%, and Boeing 737 MAX 8 at 8.59%.
What is the most popular airline from Denver to Chicago?
Based on momondo bookings for flights between Denver and Chicago, the leading airline is Frontier, making up 30% of the total bookings. Other popular airlines include United Airlines with 29%, American Airlines with 24%, and Southwest with 16%.
Best airlines flying from Denver to Chicago
Compare and see reviews for airlines that fly from Denver to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $82 | Free Cancellation | Rating 5.6 2,550 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $170 | Free Cancellation | Rating 7.9 4,223 reviews | |||
| PriceFrom $175 | Free Cancellation | Rating 7.0 12,145 reviews | |||
| PriceFrom $188 | Free Cancellation | Rating 7.4 10,319 reviews |
Southwest Flights From Denver to Chicago
The lowest priced Southwest flight from Denver to Chicago from the last 72 hours was $170. Generally, Southwest has 64 flights on this route every week with an average price of $329. Southwest is rated 7.9/10 by our users.
United Airlines Flights From Denver to Chicago
Across 10,319 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Denver to Chicago about 102 times each week, with ticket deals ranging from $188 to $382. Price data is based on momondo searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Denver to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Denver to Chicago for you.
Can I find flights from Denver to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Denver with this policy.
How can momondo help me find flights from Denver to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Denver.
I’m not ready to book a flight from Denver to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Denver and alert you when they change.