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Breckenridge

$68+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Nov 18 — Nov 251
Tue 11/18
Tue 11/25
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Breckenridge are usually found in November or September, booked 30 days in advance, depart on a Saturday or Wednesday and return on a Thursday

Find 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 October 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Mon 11/38:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/17$92
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 11/136:00 amORD - DEN
Nonstop2h 41mFrontier
Mon 11/178:44 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 10/18$93
This Priceline deal was found by Cheapflights users on 10/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:30 pmMDW - DEN
Nonstop2h 46mFrontier
Mon 11/178:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/18$93
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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.
Fri 11/146:00 amORD - DEN
Nonstop2h 41mFrontier
Mon 11/178:44 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 10/19$94
This CheapOair deal was found by Cheapflights users on 10/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Mon 11/178:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/17$94
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/114:57 pmORD - DEN
1 stop9h 11mMultiple Airlines
Thu 11/138:44 pmDEN - ORD
Nonstop2h 31mMultiple Airlines
Deal found 10/16$95
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Sun 11/25:00 amORD - DEN
Nonstop2h 41mFrontier
Sat 11/87:59 pmDEN - ORD
Nonstop2h 30mFrontier
Deal found 10/17$96
This Frontier deal was found by Cheapflights users on 10/19. 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 12/147:00 amORD - DEN
Nonstop2h 56mFrontier
Mon 12/298:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 10/19$97
This Frontier deal was found by Cheapflights users on 10/19. 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 12/1412:18 pmMDW - DEN
Nonstop2h 44mFrontier
Sun 12/286:27 pmDEN - MDW
Nonstop2h 23mFrontier
Deal found 10/19$97
This CheapOair deal was found by Cheapflights users on 10/19. 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 11/116:05 pmORD - DEN
Nonstop2h 54mFrontier
Sun 11/1612:59 amDEN - ORD
1 stop8h 42mFrontier
Deal found 10/19$99
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:36 amMDW - DEN
1 stop7h 39mFrontier
Sun 11/98:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/18$99
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/66:00 amORD - DEN
Nonstop2h 41mFrontier
Sun 11/912:59 amDEN - ORD
1 stop8h 42mFrontier
Deal found 10/17$100

Cheap flight deals from Chicago to Breckenridge

Keep the following information in mind while searching for Chicago to Breckenridge flight deals. Data was last updated October 19, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$92
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$197
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 19, 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

Sun 1/18

10:05 am-11:50 am

Nonstop2h 45m

Denver Intl

Sun 2/1

5:25 am-8:55 am

Nonstop2h 30m

$150

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 1/20

5:35 pm-7:20 pm

Nonstop2h 45m

Denver Intl

Sat 1/24

5:30 am-9:00 am

Nonstop2h 30m

$150

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 1/14

6:00 am-7:50 am

Nonstop2h 50m

Denver Intl

Tue 1/20

3:35 pm-10:50 pm

1 stop6h 15m

$160

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Thu 12/25

1:00 pm-7:15 pm

1 stop7h 15m

Denver Intl

Wed 12/31

7:30 am-3:25 pm

1 stop6h 55m

$165

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 1/24

9:45 am-1:15 pm

1 stop4h 30m

Denver Intl

Sat 1/31

1:05 pm-4:25 pm

Nonstop2h 20m

$182

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 11/15

8:20 am-10:00 am

Nonstop2h 40m

Denver Intl

Tue 11/18

4:45 pm-8:05 pm

Nonstop2h 20m

$188

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 11/26

9:30 pm-11:15 pm

Nonstop2h 45m

Denver Intl

Tue 12/2

8:30 pm-11:59 pm

Nonstop2h 29m

$191

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Thu 1/8

7:00 am-2:11 pm

1 stop8h 11m

Denver Intl

Mon 1/12

6:45 am-12:41 pm

1 stop4h 56m

$197

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 12/13

1:50 pm-8:02 pm

1 stop7h 12m

Denver Intl

Tue 12/16

11:12 am-6:18 pm

1 stop6h 06m

$197

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Fri 1/23

9:30 am-2:11 pm

1 stop5h 41m

Denver Intl

Mon 1/26

12:59 am-9:56 am

1 stop7h 57m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 42 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 October 17, 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 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 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 $112). 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 October 19, 2025.

It’s typically best to fly out from Chicago to Breckenridge in the afternoon. Doing so could potentially save you 31% on the flight price compared to flying at noon, 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 October 27, 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 October 19, 2025.

The most flights from CHI to BK9 are scheduled on a Sunday (74 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (41 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 October 19, 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
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,992 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
11,027 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.8
Fair
3,131 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $150, Southwest can have you in Breckenridge from Chicago in 2h 45m. Airlines will cover a distance of 893 mi. This flight may include one or multiple stops.

  • 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 $68 on Frontier. Other airlines that offer cheap prices include Southwest from $73 and United Airlines from $73 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 Frontier (83%), Southwest (80%) or Copa Airlines (79%) 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 $78. On average you can expect to pay $889. The most popular route, (Chicago O'Hare Intl - Denver Intl), can usually be booked for $75.

  • 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 $112). 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

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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 October 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$159FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$152Average$380FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$316FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$159Average$452FlexibilityNo cancel feeOn-time69%

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