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Breckenridge

$66+ Cheap flights from Chicago (CHI) to Breckenridge, CO

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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Breckenridge are usually found in January or October, booked 35 days in advance, depart on a Wednesday or Saturday and return on a Friday

Cheap flight deals from Chicago to Breckenridge

Cheapest flights from Chicago to Breckenridge
Explore the most affordable flight options available from Chicago to Breckenridge. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/236:50 amORD - DEN
1 stop8h 25mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$173
This Super.com deal was found by Cheapflights users on 12/19. 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.
Tue 12/236:50 amORD - DEN
1 stop8h 25mFrontier
Thu 12/258:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$195
This eDestinos deal was found by Cheapflights users on 12/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:50 amORD - DEN
1 stop8h 25mFrontier
Fri 12/268:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$196
This Expedia deal was found by Cheapflights users on 12/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:25 amORD - DEN
1 stop9h 50mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$200
This Kiwi.com deal was found by Cheapflights users on 12/19. 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.
Wed 12/316:05 pmORD - DEN
1 stop15h 43mMultiple Airlines
Thu 1/18:45 pmDEN - ORD
Nonstop2h 27mMultiple Airlines
Deal found 12/19$203
This eDestinos deal was found by Cheapflights users on 12/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:50 amORD - DEN
1 stop8h 25mFrontier
Mon 12/295:48 pmDEN - ORD
1 stop5h 06mFrontier
Deal found 12/19$212
This Super.com deal was found by Cheapflights users on 12/19. 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.
Fri 12/267:00 amORD - DEN
Nonstop2h 56mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$219
This Cheapflightsfares deal was found by Cheapflights users on 12/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:25 amORD - DEN
1 stop9h 50mFrontier
Thu 1/18:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$230
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/236:50 amORD - DEN
1 stop8h 25mFrontier
Thu 1/18:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/19$233
This Southwest deal was found by Cheapflights users on 12/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:15 amMDW - DEN
1 stop4h 55mSouthwest
Wed 12/3110:20 amDEN - MDW
1 stop5h 35mSouthwest
Deal found 12/18$242
This CheapOair deal was found by Cheapflights users on 12/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:01 pmMDW - DEN
Nonstop2h 45mFrontier
Thu 1/86:00 amDEN - MDW
1 stop31h 06mFrontier
Deal found 12/19$267
This Frontier deal was found by Cheapflights users on 12/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:01 pmMDW - DEN
1 stop10h 24mFrontier
Mon 12/2910:29 pmDEN - MDW
1 stop10h 50mFrontier
Deal found 12/19$283

Find flight deals from Chicago to Breckenridge

Keep the following information in mind while searching for Chicago to Breckenridge flight deals. Data was last updated December 21, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$105
(Super.com)

One-way from

$66
(Southwest)

Popular in

December

Cheapest in

January

Average price

$273
Provider with most accurate pricing for Chicago (CHI)-Denver Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Denver Intl flights.
Search Deals
From Chicago (CHI) to Breckenridge
Search Deals
One-way flight from Chicago (CHI) to Breckenridge
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Breckenridge 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 21, 2025.
Use the filters below to find and compare flights from Chicago to Breckenridge that are best for you.

Fly from

Chicago

Fly to

Breckenridge

Route

Depart

Return

Price

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 1/20

2:10 pm-3:50 pm

Nonstop2h 40m

Denver Intl

Sat 1/24

1:05 pm-4:25 pm

Nonstop2h 20m

$160

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 1/10

7:40 pm-9:25 pm

Nonstop2h 45m

Denver Intl

Sat 1/17

8:20 am-11:45 am

Nonstop2h 25m

$163

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 1/17

10:40 am-4:10 pm

1 stop6h 30m

Denver Intl

Tue 1/20

10:15 am-4:25 pm

1 stop5h 10m

$164

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 1/10

10:40 am-12:38 pm

Nonstop2h 58m

Denver Intl

Sat 1/17

6:00 am-9:44 am

Nonstop2h 44m

$176

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 1/27

8:10 am-12:15 pm

1 stop5h 05m

Denver Intl

Sat 1/31

8:20 am-11:45 am

Nonstop2h 25m

$176

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 2/18

9:15 pm-11:06 pm

Nonstop2h 51m

Denver Intl

Sun 2/22

6:00 am-9:38 am

Nonstop2h 38m

$177

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 1/10

8:35 am-10:30 am

Nonstop2h 55m

Denver Intl

Mon 1/12

11:00 am-4:50 pm

1 stop4h 50m

$189

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Mon 2/23

5:50 pm-7:48 pm

Nonstop2h 58m

Denver Intl

Fri 2/27

6:00 am-9:38 am

Nonstop2h 38m

$196

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Thu 1/22

2:36 pm-4:34 pm

Nonstop2h 58m

Denver Intl

Sun 1/25

6:00 am-9:44 am

Nonstop2h 44m

$196

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 2/11

9:53 am-4:41 pm

1 stop7h 48m

Denver Intl

Sat 2/14

6:00 am-3:21 pm

1 stop8h 21m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 44 results
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Best time to book a flight from Chicago to Breckenridge

Have a flexible travel schedule? Discover the best time to fly to Breckenridge from Chicago 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 Chicago to Breckenridge

How far ahead should I book a flight from Chicago to Breckenridge?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Breckenridge. Price data was last updated on December 12, 2025.

The price you pay for your flight from Chicago to Breckenridge may vary depending on when you book. For the best chance of a lower fare, look to book 35 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 Chicago to Breckenridge?

Currently, March is the cheapest month in which you can book a flight from Chicago to Breckenridge (average of $52). Flying from Chicago to Breckenridge in July is currently the most expensive (average of $115). 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 CHI to BK9?

Find hourly flight availability from Chicago to Breckenridge. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

It’s typically best to fly out from Chicago to Breckenridge in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to Breckenridge?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Breckenridge. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Breckenridge flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Breckenridge

Explore weekly flight availability from Chicago to Breckenridge. 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 21, 2025.

The most flights from CHI to BK9 are scheduled on a Friday (63 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (18 on average).

How much does it cost to fly round-trip from Chicago to Breckenridge?

Reviews of airlines servicing Breckenridge

Get insights into the airlines that provide service to Breckenridge. 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 Breckenridge. Reviews last updated December 21, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Breckenridge have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
9,099 reviews
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
11,050 reviews
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
5.8
Fair
3,082 reviews
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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 Chicago to Breckenridge. 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 Chicago to Breckenridge?

    For as low as $160, Frontier can have you in Breckenridge from Chicago in 2h 40m. Airlines will cover a distance of 893 mi. All flights are typically nonstop.

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

    One-way options have recently been found by users for as low as $38 on Frontier. Other airlines that offer cheap prices include Southwest from $76 and American Airlines from $79 one-way.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Breckenridge consider choosing Qatar Airways (80%), American Airlines (77%) or Iberia (74%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Breckenridge?

    The cheapest flight price from Chicago to Breckenridge is $63. On average you can expect to pay $748. The most popular route, (Chicago O'Hare Intl - Denver Intl), can usually be booked for $117.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Breckenridge 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 Chicago to Breckenridge?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Breckenridge (average of $52). Flying from Chicago to Breckenridge in July is currently the most expensive (average of $115). 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

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 Chicago to Breckenridge

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Breckenridge

Discover the top 4 airlines that operate flights from Chicago to Breckenridge. 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$160FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$153Average$345FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$155Average$432FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$303FlexibilityNo cancel feeOn-time63%

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