Frontier's UpFront Plus offers a guaranteed empty middle seat for extra comfort.
Early check-in helps secure your place as Frontier often overbooks flights.
$83+ Cheap flights from Denver (DEN) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jul 3 — Jul 101
1 adult, Economy
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Find cheap flights from Denver to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Denver Intl to Chicago are usually found in September or October, booked 30 days in advance, depart on a Friday or Thursday and return on a Wednesday
Cheap flight deals from Denver to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Denver (DEN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 28, 2025.
Round-trip from | $158 (CheapOair) |
|---|---|
One-way from | $83 (CheapOair) |
Popular in | May |
Cheapest in | September |
Average price | $215 |
Good round-trip deal | $201 or less |
Good one-way deal | $120 or less |
Find flight deals from Denver to Chicago
Cheapest flights from Denver to ChicagoExplore the most affordable flight options available from Denver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 28, 2025.
Explore the most affordable flight options available from Denver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 28, 2025.
This CheapOair deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:30 amDEN - ORD
1 stop8h 44mFrontier
Mon 8/49:56 pmORD - DEN
1 stop18h 22mFrontier
Deal found 6/27![Frontier logo]()
$158
This CheapOair deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/246:06 amDEN - MDW
1 stop6h 23mFrontier
Sun 7/273:58 pmMDW - DEN
1 stop8h 58mFrontier
Deal found 6/28![Frontier logo]()
$159
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/314:55 pmDEN - MDW
Nonstop2h 20mSouthwest
Mon 9/15:25 amMDW - DEN
Nonstop2h 35mSouthwest
Deal found 6/27![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:35 amDEN - ORD
Nonstop2h 30mSouthwest
Tue 8/197:30 amORD - DEN
2 stops9h 00mSouthwest
Deal found 6/27![Southwest logo]()
$172
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/257:18 amDEN - ORD
Nonstop2h 32mAmerican Airlines
Mon 7/286:48 amORD - DEN
Nonstop2h 34mAmerican Airlines
Deal found 6/27![American Airlines logo]()
$201
This Mytrip deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/254:05 pmDEN - RFD
2 stops15h 07mMultiple Airlines
Sun 7/279:21 amRFD - DEN
2 stops23h 14mMultiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$368
This Mytrip deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:54 amDEN - RFD
2 stops22h 10mAllegiant Air
Sun 10/1210:14 amRFD - DEN
2 stops22h 37mAllegiant Air
Deal found 6/26![Allegiant Air logo]()
$459
Cheapflights Fare Finder
Customize your flight search to find flights from Denver to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 28, 2025.
Use the filters below to find and compare flights from Denver to Chicago that are best for you.
Fly from
Denver
Fly to
Chicago
Route
Depart
Return
Price
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 8/2
6:30 am-4:14 pm
1 stop8h 44m
Chicago O'Hare Intl
Mon 8/4
9:56 pm-3:18 pm
1 stop18h 22m
$158
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 7/24
6:06 am-1:29 pm
1 stop6h 23m
Chicago Midway
Sun 7/27
3:58 pm-11:56 pm
1 stop8h 58m
$159
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sun 8/31
4:55 pm-8:15 pm
Nonstop2h 20m
Chicago Midway
Mon 9/1
5:25 am-7:00 am
Nonstop2h 35m
$168
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 8/14
10:35 am-2:05 pm
Nonstop2h 30m
Chicago O'Hare Intl
Tue 8/19
7:30 am-3:30 pm
2 stops9h 00m
$172
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 7/25
5:32 pm-9:22 pm
Nonstop2h 50m
Chicago O'Hare Intl
Mon 7/28
8:45 pm-10:47 pm
Nonstop3h 02m
$201
DenverChicago
DEN - RFD
DENRFD
Denver Intl
Fri 7/25
4:05 pm-8:12 am
2 stops15h 07m
Chicago Greater Rockford
Sun 7/27
9:21 am-7:35 am
2 stops23h 14m
$368
DenverChicago
DEN - RFD
DENRFD
Denver Intl
Thu 10/9
8:54 am-8:04 am
2 stops22h 10m
Chicago Greater Rockford
Sun 10/12
10:14 am-7:51 am
2 stops22h 37m
$459
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 8/6
6:50 am-12:49 pm
1 stop28h 59m
$83
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 8/4
6:50 am-10:23 pm
1 stop14h 33m
$83
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 10/16
4:15 pm-7:55 pm
Nonstop2h 40m
$85
Showing 1-10 of 18 results
The best insider tips for Denver to Chicago flights
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Denver to Chicago trip
Airlines
![Frontier]()
Frontier
![United Airlines]()
United Airlines
Basic Economy allows only a personal item; no carry-on bags unless exceptions apply.
United Club access includes healthy snacks and comfortable seating, but may be limited when full.
Airports
Our travel experts
Best time to book a flight from Denver to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Denver with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Denver to Chicago
How far ahead should I book a flight from Denver to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Denver to Chicago. Price data was last updated on June 20, 2025.
The price you pay for your flight from Denver to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Denver to Chicago?
Currently, August is the cheapest month in which you can book a flight from Denver to Chicago (average of $245). Flying from Denver to Chicago in March is currently the most expensive (average of $320). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from DEN to CHI?
Find hourly flight availability from Denver to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 28, 2025.
It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 72% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Denver to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Denver to Chicago. Price data was last updated on June 22, 2025.
Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Denver to Chicago
Explore weekly flight availability from Denver to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 28, 2025.
The most flights from DEN to CHI are scheduled on a Friday (75 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (41 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 28, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Denver to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.6
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Entertainment
7.6
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Entertainment
7.6
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Entertainment
7.6
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Entertainment
7.6
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Entertainment
7.6
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.2
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Denver to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Denver?
Book flights to Denver if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton
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Alternative routes for Denver to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Denver to Chicago
Discover the top 4 airlines that operate flights from Denver to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 28, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$54 | Average$154 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$150 | Average$232 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$155 | Average$250 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$304 | FlexibilityNo cancel fee | On-time69% |