HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$80+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
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 February or August, booked 79 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Breckenridge to Chicago

Cheapest flights from Breckenridge to Chicago
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 January 20, 2026.

This Frontier deal was found by Cheapflights users on 1/17. 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 2/208:24 am
DEN
-
ORD
Nonstop2h 34m
Frontier
Tue 2/2411:51 am
ORD
-
DEN
1 stop10h 50m
Frontier
Deal found 1/17$108
This CheapOair deal was found by Cheapflights users on 1/18. 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.
Wed 2/1812:05 pm
DEN
-
ORD
1 stop23h 49m
Frontier
Fri 2/2012:53 pm
ORD
-
DEN
Nonstop2h 58m
Frontier
Deal found 1/18$109
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 3/108:17 am
DEN
-
ORD
1 stop5h 58m
Frontier
Fri 3/136:30 pm
ORD
-
DEN
Nonstop3h 04m
Frontier
Deal found 1/19$110
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Sat 3/710:20 am
DEN
-
ORD
1 stop13h 01m
Frontier
Mon 3/96:30 pm
ORD
-
DEN
Nonstop3h 04m
Frontier
Deal found 1/19$112
This CheapOair deal was found by Cheapflights users on 1/20. 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 2/127:35 pm
DEN
-
ORD
Nonstop2h 39m
Frontier
Thu 2/1911:41 am
ORD
-
DEN
1 stop12h 36m
Frontier
Deal found 1/20$113
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Thu 2/197:35 pm
DEN
-
ORD
Nonstop2h 39m
Frontier
Mon 2/237:45 am
ORD
-
DEN
1 stop27h 12m
Frontier
Deal found 1/18$115
This Cheapflightsfares deal was found by Cheapflights users on 1/18. 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 3/57:35 pm
DEN
-
ORD
Nonstop2h 39m
Frontier
Sat 3/77:00 am
ORD
-
DEN
1 stop12h 08m
Frontier
Deal found 1/18$117
This Cheapflightsfares deal was found by Cheapflights users on 1/18. 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.
Fri 3/69:29 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Tue 3/108:55 pm
ORD
-
DEN
1 stop23h 59m
Frontier
Deal found 1/18$118
This Kiwi.com deal was found by Cheapflights users on 1/17. 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.
Thu 2/197:35 pm
DEN
-
ORD
Nonstop2h 39m
Frontier
Sat 2/216:20 am
ORD
-
DEN
1 stop12h 03m
Frontier
Deal found 1/17$121
This Cheapflightsfares deal was found by Cheapflights users on 1/18. 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.
Fri 2/279:41 am
DEN
-
ORD
Nonstop2h 44m
Frontier
Mon 3/27:35 am
ORD
-
DEN
1 stop25h 51m
Frontier
Deal found 1/18$123
This Super.com deal was found by Cheapflights users on 1/19. 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.
Thu 3/57:35 pm
DEN
-
ORD
Nonstop2h 39m
Frontier
Mon 3/96:30 pm
ORD
-
DEN
Nonstop3h 04m
Frontier
Deal found 1/19$124
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Tue 2/171:42 pm
DEN
-
MDW
1 stop28h 25m
Frontier
Tue 2/246:10 am
MDW
-
DEN
1 stop16h 31m
Frontier
Deal found 1/18$128

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 January 20, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$108
(Frontier)

One-way from

$80
(Cheapflightsfares)

Popular in

November

Cheapest in

February

Average price

$208
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
Search Deals
From Breckenridge to Chicago (CHI)
Search Deals
One-way flight from Breckenridge to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 20, 2026.
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

Wed 2/18

7:24 pm-10:53 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sat 2/21

12:50 pm-2:48 pm

Nonstop2h 58m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 3/4

1:25 pm-4:45 pm

Nonstop2h 20m

Chicago Midway

Thu 3/5

5:40 am-7:25 am

Nonstop2h 45m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 2/18

7:00 am-2:20 pm

1 stop6h 20m

Chicago Midway

Wed 2/18

4:25 pm-9:05 pm

1 stop5h 40m

$177

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 4/1

6:10 pm-12:05 am

1 stop4h 55m

Chicago Midway

Sat 4/4

6:50 pm-12:20 am

1 stop6h 30m

$187

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 2/18

1:45 pm-10:35 pm

1 stop7h 50m

Chicago O'Hare Intl

Sat 2/21

5:15 pm-7:05 pm

Nonstop2h 50m

$189

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 4/9

5:35 pm-9:05 pm

Nonstop2h 30m

Chicago Midway

Mon 4/13

9:35 pm-11:15 pm

Nonstop2h 40m

$191

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 3/6

11:30 am-3:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 3/9

6:25 pm-8:15 pm

Nonstop2h 50m

$194

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 2/19

7:45 am-11:19 am

Nonstop2h 34m

Chicago O'Hare Intl

Mon 2/23

9:15 pm-11:06 pm

Nonstop2h 51m

$195

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 3/12

6:20 am-9:45 am

Nonstop2h 25m

Chicago Midway

Sun 3/15

5:55 am-7:40 am

Nonstop2h 45m

$200

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 3/11

10:10 am-1:55 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 3/18

6:15 am-12:25 pm

1 stop7h 10m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 55 results
1
2
3
...
6

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 January 16, 2026.

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, February is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $60). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $123). 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 January 20, 2026.

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 January 17, 2026.

Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Saturday 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 January 20, 2026.

The most flights from BK9 to CHI are scheduled on a Monday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 January 20, 2026.
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.
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,184 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,166 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Breckenridge to Chicago?

    For as low as $167, United Airlines can have you in Chicago from Breckenridge in 2h 20m. The distance from Breckenridge to Chicago is about 893 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Breckenridge to Chicago one-way?

    One-way options have recently been found by users for as low as $40 on Frontier. Other airlines that offer cheap prices include Southwest from $78 and American Airlines from $78 one-way.

  • What are the most popular routes from Breckenridge to Chicago?

    The most popular route from Breckenridge to Chicago is Denver Intl - Chicago O'Hare Intl. You may also consider Denver Intl - Chicago Midway or Denver Intl - Chicago Greater Rockford.

  • What are the most reliable airlines from Breckenridge to Chicago?

    Before booking your flight to Chicago from Breckenridge, check out the most reliable airlines to get you to your destination on time: Copa Airlines (89%), Austrian Airlines (86%), Brussels Airlines( 77%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $667 for a flight from Breckenridge to Chicago. The cheapest flight overall is $82 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $86.

  • Can I find deals for flights from Breckenridge to Chicago that include hotel bookings?

    Yes. In addition to deals on Breckenridge to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Breckenridge to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Breckenridge to Chicago.

  • Can I find deals for business class flights from Breckenridge to Chicago?

    Yes. Cheapflights offers flight deals from Breckenridge to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Breckenridge to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $60). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $123). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
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.
Denver to O'Hare Intl flights
Denver to Midway flights
Denver to St. Louis flights
Colorado Springs to O'Hare Intl flights
Denver to Moline flights
Denver to Peoria flights
Colorado Springs to Midway flights
Vail to O'Hare Intl flights
Denver to Rockford flights
Grand Junction to O'Hare Intl flights
Montrose to O'Hare Intl flights
Gunnison to O'Hare Intl flights
Colorado Springs to St. Louis flights
Aspen to O'Hare Intl flights
Hayden to O'Hare Intl flights
Durango to O'Hare Intl flights
Vail to Midway flights
Grand Junction to Midway flights
Aspen to Midway flights
Denver to Bloomington flights
Colorado Springs to Peoria flights
Montrose to Midway flights
Montrose to Peoria flights
Montrose to St. Louis flights
Denver to Springfield flights
Colorado Springs to Moline flights
Aspen to St. Louis flights
Durango to St. Louis flights
Denver to Evansville flights
Denver to Champaign flights
Colorado Springs to Springfield flights
Grand Junction to St. Louis flights
Hayden to St. Louis flights
Gunnison to St. Louis flights
Grand Junction to Bloomington flights
Vail to St. Louis flights
Denver to Decatur flights
Grand Junction to Peoria flights
Hayden to Moline flights
Denver to Dubuque flights
Colorado Springs to Evansville flights
Durango to Moline flights
Durango to Midway flights
Colorado Springs to Champaign flights
Colorado Springs to Bloomington flights
Montrose to Springfield flights

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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$171FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$155Average$279FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$156Average$393FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$372FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.