$72+ Cheap flights from Breckenridge, CO 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jan 27 — Feb 31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Breckenridge 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 Breckenridge to Chicago are usually found in January or February, booked 79 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Breckenridge to Chicago
Cheapest flights from Breckenridge to ChicagoExplore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.
Explore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sun 1/410:49 pmORD - DEN
1 stop25h 39mFrontier
Deal found 12/26![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 12/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Tue 1/611:59 amORD - DEN
1 stop6h 41mFrontier
Deal found 12/25![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sat 1/37:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/26![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:42 pmDEN - MDW
1 stop6h 30mFrontier
Fri 1/93:05 pmMDW - DEN
Nonstop2h 49mFrontier
Deal found 12/26![Frontier logo]()
$291
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/94:30 pmORD - DEN
Nonstop3h 01mFrontier
Deal found 12/26![Frontier logo]()
$293
This Super.com deal was found by Cheapflights users on 12/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:59 pmDEN - ORD
1 stop9h 19mFrontier
Thu 1/17:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/25![Frontier logo]()
$306
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:36 pmDEN - MDW
Nonstop2h 19mFrontier
Mon 1/53:10 pmMDW - DEN
1 stop8h 54mFrontier
Deal found 12/26![Frontier logo]()
$311
This CheapOair deal was found by Cheapflights users on 12/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:36 pmDEN - MDW
Nonstop2h 19mFrontier
Wed 1/73:01 pmMDW - DEN
1 stop25h 41mFrontier
Deal found 12/26![Frontier logo]()
$313
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:45 pmDEN - ORD
Nonstop2h 27mFrontier
Mon 1/57:25 amORD - DEN
1 stop9h 45mFrontier
Deal found 12/26![Frontier logo]()
$319
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:59 pmDEN - ORD
1 stop9h 19mFrontier
Wed 1/75:29 pmORD - DEN
1 stop30h 30mFrontier
Deal found 12/26![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:29 pmDEN - ORD
1 stop20h 54mMultiple Airlines
Tue 1/67:57 pmORD - DEN
1 stop16h 29mMultiple Airlines
Deal found 12/25![Multiple Airlines logo]()
$333
This Expedia deal was found by Cheapflights users on 12/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 amDEN - MDW
1 stop5h 59mFrontier
Tue 1/62:03 pmMDW - DEN
1 stop8h 32mFrontier
Deal found 12/25![Frontier logo]()
$372
Find flight deals from Breckenridge to Chicago
Keep the following information in mind while searching for Breckenridge to Chicago flight deals. Data was last updated December 28, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $106 (Kiwi.com) |
One-way from | $72 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $251 |
Cheapflights Fare Finder
Customize your flight search to find flights from Breckenridge 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 December 28, 2025.
Use the filters below to find and compare flights from Breckenridge to Chicago that are best for you.
Fly from
Breckenridge
Fly to
Chicago
Route
Depart
Return
Price
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 2/20
8:24 am-11:58 am
Nonstop2h 34m
Chicago O'Hare Intl
Wed 2/25
8:30 am-10:59 pm
1 stop15h 29m
$115
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 2/12
7:35 pm-11:14 pm
Nonstop2h 39m
Chicago O'Hare Intl
Fri 2/20
9:17 pm-7:54 am
1 stop11h 37m
$121
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 1/17
9:02 pm-1:20 pm
1 stop15h 18m
Chicago O'Hare Intl
Mon 1/19
2:30 pm-4:41 pm
Nonstop3h 11m
$151
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 2/11
6:30 am-5:03 pm
1 stop9h 33m
Chicago O'Hare Intl
Wed 2/18
11:51 am-9:35 pm
1 stop10h 44m
$152
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 1/16
5:41 pm-9:24 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 1/19
1:57 pm-9:11 pm
1 stop8h 14m
$155
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 1/29
4:14 pm-11:22 am
3 stops18h 08m
Chicago O'Hare Intl
Sun 2/1
12:07 pm-2:05 pm
Nonstop2h 58m
$179
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 1/29
6:30 am-5:52 pm
2 stops10h 22m
Chicago O'Hare Intl
Fri 1/30
12:42 pm-8:20 pm
1 stop8h 38m
$181
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 1/15
2:20 pm-7:45 pm
1 stop4h 25m
Chicago Midway
Sun 1/18
8:10 am-10:00 am
Nonstop2h 50m
$182
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sun 1/25
9:12 pm-5:52 pm
2 stops19h 40m
Chicago O'Hare Intl
Sun 2/1
12:07 pm-2:05 pm
Nonstop2h 58m
$183
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 2/26
8:30 pm-11:59 pm
Nonstop2h 29m
Chicago O'Hare Intl
Sat 2/28
5:50 pm-7:48 pm
Nonstop2h 58m
$187
Showing 1-10 of 55 results
Best time to book a flight from Breckenridge to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Breckenridge 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 Breckenridge to Chicago
How far ahead should I book a flight from Breckenridge to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Breckenridge to Chicago. Price data was last updated on December 26, 2025.
The price you pay for your flight from Breckenridge to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 79 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 Breckenridge to Chicago?
Currently, January is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $58). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $122). 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 BK9 to CHI?
Find hourly flight availability from Breckenridge 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 December 28, 2025.
When flying from Breckenridge to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 65% versus a flight at noon.
What is the cheapest day to fly from Breckenridge to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Breckenridge to Chicago. Price data was last updated on December 27, 2025.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Breckenridge to Chicago
Explore weekly flight availability from Breckenridge 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 December 28, 2025.
The most flights from BK9 to CHI are scheduled on a Friday (66 on average). You will have fewer flight options on Wednesday, 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 December 28, 2025.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Breckenridge 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Breckenridge to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Breckenridge to Chicago
Discover the top 4 airlines that operate flights from Breckenridge 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 December 28, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$173 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$278 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$375 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$162 | Average$395 | FlexibilityNo cancel fee | On-time69% |