$59+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jan 3 — Jan 101
1 adult, Economy
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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 67 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 4, 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 4, 2025.
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/248:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/96:07 pmORD - DEN
1 stop24h 56mFrontier
Deal found 12/2![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 12/4. 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.
Sun 12/219:00 pmDEN - ORD
1 stop25h 54mFrontier
Thu 1/87:50 pmORD - DEN
Nonstop2h 59mFrontier
Deal found 12/4![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 12/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 pmDEN - ORD
Nonstop2h 27mFrontier
Thu 1/87:50 pmORD - DEN
Nonstop2h 59mFrontier
Deal found 12/4![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Wed 1/74:49 pmORD - DEN
1 stop29h 49mFrontier
Deal found 12/4![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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
Mon 1/51:32 pmORD - DEN
1 stop11h 53mFrontier
Deal found 12/3![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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 1/36:17 pmORD - DEN
1 stop6h 20mFrontier
Deal found 12/2![Frontier logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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.
Thu 12/258:45 pmDEN - ORD
Nonstop2h 27mFrontier
Tue 12/307:01 pmORD - DEN
1 stop14h 23mFrontier
Deal found 12/1![Frontier logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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 12/248:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/29:31 pmORD - DEN
1 stop10h 44mFrontier
Deal found 12/3![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 12/4. 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 1/47:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/4![Frontier logo]()
$122
This deal was found by Cheapflights users on 12/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:45 pmDEN - ORD
Nonstop2h 27mFrontier
Mon 12/87:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/2![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/248:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sat 1/36:17 pmORD - DEN
1 stop6h 20mFrontier
Deal found 12/2![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 12/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1910:46 amDEN - ORD
1 stop11h 00mFrontier
Thu 1/87:50 pmORD - DEN
Nonstop2h 59mFrontier
Deal found 12/4![Frontier logo]()
$130
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 4, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $95 (Super.com) |
One-way from | $59 (United Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $205 |
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 4, 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
Mon 1/12
5:42 pm-9:15 pm
Nonstop2h 33m
Chicago O'Hare Intl
Wed 1/14
7:00 am-8:49 am
Nonstop2h 49m
$105
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 1/14
6:45 am-1:00 pm
1 stop5h 15m
Chicago O'Hare Intl
Wed 1/21
1:45 pm-7:20 pm
1 stop6h 35m
$113
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 1/24
7:50 am-11:34 am
Nonstop2h 44m
Chicago O'Hare Intl
Sat 1/24
6:15 pm-8:12 pm
Nonstop2h 57m
$117
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 1/24
7:50 am-11:34 am
Nonstop2h 44m
Chicago O'Hare Intl
Mon 1/26
12:53 pm-2:51 pm
Nonstop2h 58m
$117
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 1/28
6:45 am-1:00 pm
1 stop5h 15m
Chicago O'Hare Intl
Mon 2/2
2:15 pm-10:40 pm
2 stops9h 25m
$155
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 1/6
6:25 pm-9:50 pm
Nonstop2h 25m
Chicago Midway
Fri 1/9
2:10 pm-3:50 pm
Nonstop2h 40m
$155
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 1/15
7:05 pm-10:25 pm
Nonstop2h 20m
Chicago Midway
Sun 1/18
8:10 am-10:00 am
Nonstop2h 50m
$157
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 1/23
10:35 am-4:35 pm
1 stop5h 00m
Chicago Midway
Mon 1/26
7:55 pm-9:40 pm
Nonstop2h 45m
$159
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 1/6
6:00 am-9:43 am
Nonstop2h 43m
Chicago O'Hare Intl
Wed 1/14
2:36 pm-4:34 pm
Nonstop2h 58m
$163
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 1/15
7:05 pm-10:25 pm
Nonstop2h 20m
Chicago Midway
Mon 1/19
11:20 am-1:05 pm
Nonstop2h 45m
$171
Showing 1-10 of 57 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 November 28, 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 67 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 4, 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 60% 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 16, 2024.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Tuesday mornings 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 4, 2025.
The most flights from BK9 to CHI are scheduled on a Wednesday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
How much does it cost to fly round-trip from Breckenridge to Chicago?
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 4, 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.
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
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
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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 4, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$174 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$279 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$165 | Average$392 | FlexibilityNo cancel fee | On-time69% |