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$75+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in October or September, booked 69 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Breckenridge to Chicago

Keep the following information in mind while searching for Breckenridge to Chicago flight deals. Data was last updated August 11, 2025.

Round-trip from

$125
(Frontier)

One-way from

$75
(Kiwi.com)

Popular in

May

Cheapest in

October

Average price

$181
From Breckenridge to Chicago (CHI)
Search Deals
One-way flight from Breckenridge to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 11, 2025.

This Frontier deal was found by Cheapflights users on 8/10. 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 9/58:30 pmDEN - ORD
Nonstop2h 29mFrontier
Tue 9/97:20 amORD - DEN
Nonstop2h 53mFrontier
Deal found 8/10$125
This Frontier deal was found by Cheapflights users on 8/10. 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.
Thu 8/288:53 pmDEN - ORD
Nonstop2h 39mFrontier
Sun 8/316:00 amORD - DEN
Nonstop2h 48mFrontier
Deal found 8/10$126
This CheapOair deal was found by Cheapflights users on 8/9. 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 9/512:28 pmDEN - MDW
Nonstop2h 25mFrontier
Fri 9/124:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/9$126
This Frontier deal was found by Cheapflights users on 8/10. 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 10/68:30 pmDEN - ORD
Nonstop2h 29mFrontier
Sat 10/117:15 amORD - DEN
Nonstop2h 49mFrontier
Deal found 8/10$127
This Frontier deal was found by Cheapflights users on 8/10. 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 9/128:30 pmDEN - ORD
Nonstop2h 29mFrontier
Sun 9/146:00 amORD - DEN
Nonstop2h 45mFrontier
Deal found 8/10$128
This Frontier deal was found by Cheapflights users on 8/10. 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 8/317:00 amDEN - ORD
Nonstop2h 37mFrontier
Wed 9/37:20 amORD - DEN
Nonstop2h 53mFrontier
Deal found 8/10$129
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/2612:28 pmDEN - MDW
Nonstop2h 25mFrontier
Mon 9/294:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/9$129
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Sat 9/65:50 pmDEN - ORD
Nonstop2h 38mFrontier
Sun 9/76:00 amORD - DEN
Nonstop2h 45mFrontier
Deal found 8/10$130
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 10/168:22 pmDEN - ORD
Nonstop2h 31mFrontier
Sun 10/196:50 amORD - DEN
Nonstop2h 41mFrontier
Deal found 8/10$131
This Frontier deal was found by Cheapflights users on 8/10. 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 9/76:00 amDEN - ORD
Nonstop2h 37mFrontier
Thu 9/116:00 amORD - DEN
Nonstop2h 45mFrontier
Deal found 8/10$132
This Frontier deal was found by Cheapflights users on 8/9. 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 9/58:30 pmDEN - ORD
Nonstop2h 29mFrontier
Sat 9/138:25 amORD - DEN
Nonstop2h 51mFrontier
Deal found 8/9$133
This CheapOair deal was found by Cheapflights users on 8/10. 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 10/248:58 pmDEN - MDW
Nonstop2h 26mFrontier
Mon 10/276:24 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 8/10$133

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 August 11, 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

Fri 9/5

8:30 pm-11:59 pm

Nonstop2h 29m

Chicago O'Hare Intl

Wed 9/10

7:20 am-9:13 am

Nonstop2h 53m

$125

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 8/28

8:53 pm-12:32 am

Nonstop2h 39m

Chicago O'Hare Intl

Sun 8/31

6:00 am-7:48 am

Nonstop2h 48m

$126

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/5

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Fri 9/12

4:48 pm-6:26 pm

Nonstop2h 38m

$126

DenverChicago

DEN - ORD

DENORD

Denver Intl

Mon 10/6

8:30 pm-11:59 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sat 10/11

7:15 am-9:04 am

Nonstop2h 49m

$127

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 9/12

8:30 pm-11:59 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sun 9/14

6:00 am-7:45 am

Nonstop2h 45m

$128

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sun 8/31

7:00 am-10:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Wed 9/3

7:20 am-9:13 am

Nonstop2h 53m

$129

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/26

12:28 pm-3:53 pm

Nonstop2h 25m

Chicago Midway

Mon 9/29

4:48 pm-6:26 pm

Nonstop2h 38m

$129

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 9/6

5:50 pm-9:28 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sun 9/7

6:00 am-7:45 am

Nonstop2h 45m

$130

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 10/16

8:22 pm-11:53 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 10/19

6:50 am-8:31 am

Nonstop2h 41m

$131

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sun 9/7

6:00 am-9:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Thu 9/11

6:00 am-7:45 am

Nonstop2h 45m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 59 results
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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 August 8, 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 21 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, August is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $245). Flying from Breckenridge to Chicago in March is currently the most expensive (average of $321). 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 August 11, 2025.

When flying from Breckenridge to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 evenings when fares are most often at their lowest. Monday 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 August 11, 2025.

The most flights from BK9 to CHI are scheduled on a Friday (75 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (51 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 August 11, 2025.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
8,920 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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 Breckenridge to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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: Japan Airlines (84%), Turkish Airlines (84%), Cathay Pacific( 80%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $899 for a flight from Breckenridge to Chicago. The cheapest flight overall is $77 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $112.

  • 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, August is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $245). Flying from Breckenridge to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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.
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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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$158FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$154Average$292FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$154Average$352FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$164Average$419FlexibilityNo cancel feeOn-time69%

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