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Breckenridge

$70+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 Wednesday or Saturday 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 November 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Thu 12/47:00 amORD - DEN
Nonstop2h 56mFrontier
Fri 12/512:59 amDEN - ORD
1 stop9h 55mFrontier
Deal found 11/2$94
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:00 amORD - DEN
Nonstop2h 56mFrontier
Mon 12/158:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/3$95
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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.
Fri 12/56:00 amORD - DEN
1 stop27h 24mFrontier
Mon 12/88:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/1$96
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:00 amORD - DEN
Nonstop2h 56mFrontier
Thu 12/188:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/3$97
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:00 amORD - DEN
Nonstop2h 56mFrontier
Mon 12/812:59 amDEN - ORD
1 stop13h 13mFrontier
Deal found 11/2$99
This Priceline deal was found by Cheapflights users on 11/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:18 pmMDW - DEN
Nonstop2h 44mFrontier
Mon 12/86:00 amDEN - MDW
1 stop7h 52mFrontier
Deal found 11/2$99
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1511:01 amORD - DEN
1 stop11h 58mFrontier
Wed 12/248:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/2$101
This Frontier deal was found by Cheapflights users on 11/2. 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 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
Sun 12/218:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/2$102
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Mon 12/157:00 amORD - DEN
Nonstop2h 56mFrontier
Wed 12/179:00 pmDEN - ORD
1 stop21h 21mFrontier
Deal found 11/2$103
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Fri 12/122:26 pmORD - DEN
1 stop18h 58mFrontier
Mon 12/158:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/3$104
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/243:31 pmMDW - DEN
Nonstop2h 51mFrontier
Fri 11/282:50 pmDEN - MDW
Nonstop2h 22mFrontier
Deal found 11/2$104
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:18 pmMDW - DEN
Nonstop2h 44mFrontier
Mon 12/157:45 amDEN - MDW
Nonstop2h 23mFrontier
Deal found 11/2$106

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 November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$94
(Cheapflightsfares)

One-way from

$70
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$163
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. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Fri 12/12

6:15 am-2:10 pm

1 stop8h 55m

Denver Intl

Mon 12/15

7:45 am-11:08 am

Nonstop2h 23m

$108

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sun 2/15

8:50 pm-10:35 pm

Nonstop2h 45m

Denver Intl

Fri 2/20

5:15 am-8:45 am

Nonstop2h 30m

$155

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 1/21

6:15 pm-8:13 pm

Nonstop2h 58m

Denver Intl

Sun 1/25

6:00 am-9:44 am

Nonstop2h 44m

$155

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 1/22

6:00 am-7:50 am

Nonstop2h 50m

Denver Intl

Sun 1/25

7:05 pm-10:25 pm

Nonstop2h 20m

$155

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Fri 2/13

9:35 pm-11:15 pm

Nonstop2h 40m

Denver Intl

Sun 2/15

5:25 am-8:55 am

Nonstop2h 30m

$155

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/24

7:55 pm-9:40 pm

Nonstop2h 45m

Denver Intl

Fri 2/27

6:15 pm-9:45 pm

Nonstop2h 30m

$155

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Fri 1/30

7:55 pm-9:40 pm

Nonstop2h 45m

Denver Intl

Tue 2/3

7:00 am-10:35 am

Nonstop2h 35m

$155

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/17

9:55 am-2:30 pm

1 stop5h 35m

Denver Intl

Sun 2/22

5:15 am-8:45 am

Nonstop2h 30m

$165

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 12/13

10:45 am-5:27 pm

1 stop7h 42m

Denver Intl

Tue 12/16

1:16 pm-10:43 pm

1 stop8h 27m

$197

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Tue 12/2

6:00 am-10:07 am

1 stop5h 07m

Denver Intl

Tue 12/2

4:15 pm-9:40 pm

1 stop4h 25m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 43 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 31, 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 $114). 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 November 3, 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 November 3, 2025.

The most flights from CHI to BK9 are scheduled on a Sunday (63 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 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 November 3, 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
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
11,036 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
3,117 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

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 $155, Frontier 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 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 Air Canada (84%), Copa Airlines (83%) or United Airlines (81%) 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 $81. On average you can expect to pay $658. The most popular route, (Chicago O'Hare Intl - Denver Intl), can usually be booked for $101.

  • 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 $114). 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.

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$160FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$153Average$377FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$318FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$160Average$445FlexibilityNo cancel feeOn-time69%

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