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$66+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in January or February, booked 67 days in advance, depart on a Thursday or Friday and return on a Wednesday

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 December 23, 2025.

This Super.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Mon 1/52:15 pmORD - DEN
1 stop9h 44mFrontier
Deal found 12/21$117
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sun 1/45:08 pmORD - DEN
1 stop8h 17mFrontier
Deal found 12/21$121
This Frontier deal was found by Cheapflights users on 12/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sat 1/37:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/20$122
This Frontier deal was found by Cheapflights users on 12/21. 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.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Thu 1/17:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/21$153
This Frontier deal was found by Cheapflights users on 12/21. 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.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/29:31 pmORD - DEN
1 stop10h 44mFrontier
Deal found 12/21$175
This Booking.com deal was found by Cheapflights users on 12/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amDEN - MDW
1 stop12h 45mFrontier
Mon 1/53:10 pmMDW - DEN
1 stop27h 23mFrontier
Deal found 12/21$175
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/259:00 pmDEN - ORD
1 stop18h 42mFrontier
Wed 12/317:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/22$178
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:20 amDEN - MDW
1 stop7h 29mDelta
Wed 12/313:29 pmMDW - DEN
1 stop7h 16mDelta
Deal found 12/21$197
This CheapOair deal was found by Cheapflights users on 12/21. 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 12/317:00 amDEN - MDW
1 stop12h 45mFrontier
Sun 1/43:01 pmMDW - DEN
1 stop10h 24mFrontier
Deal found 12/21$215
This Frontier deal was found by Cheapflights users on 12/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:29 pmDEN - MDW
1 stop10h 50mFrontier
Sun 1/43:01 pmMDW - DEN
1 stop10h 24mFrontier
Deal found 12/20$233
This Frontier deal was found by Cheapflights users on 12/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:36 pmDEN - MDW
Nonstop2h 19mFrontier
Sun 1/43:01 pmMDW - DEN
1 stop10h 24mFrontier
Deal found 12/20$247
This Frontier deal was found by Cheapflights users on 12/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:30 amDEN - MDW
1 stop7h 58mFrontier
Sun 1/43:01 pmMDW - DEN
1 stop10h 24mFrontier
Deal found 12/20$258

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 December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$97
(Cheapflightsfares)

One-way from

$66
(Southwest)

Popular in

November

Cheapest in

January

Average price

$251
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. 12% potential increase in price ($30 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 December 2025
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 December 23, 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 - MDW

DENMDW

Denver Intl

Sat 1/17

8:20 am-11:45 am

Nonstop2h 25m

Chicago Midway

Sat 1/17

4:05 pm-5:50 pm

Nonstop2h 45m

$147

DenverChicago

DEN - ORD

DENORD

Denver Intl

Mon 1/5

9:07 pm-10:49 am

1 stop12h 42m

Chicago O'Hare Intl

Sat 1/10

8:27 pm-10:59 pm

1 stop27h 32m

$162

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 1/8

1:42 pm-10:17 pm

1 stop7h 35m

Chicago Midway

Mon 1/12

6:10 am-12:21 pm

1 stop7h 11m

$163

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 1/7

10:29 pm-11:45 am

1 stop12h 16m

Chicago Midway

Fri 1/9

3:05 pm-4:54 pm

Nonstop2h 49m

$165

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/14

4:15 pm-7:51 pm

Nonstop2h 36m

Chicago O'Hare Intl

Tue 1/20

2:36 pm-4:34 pm

Nonstop2h 58m

$168

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/14

7:50 am-11:34 am

Nonstop2h 44m

Chicago O'Hare Intl

Sun 1/18

10:40 am-12:38 pm

Nonstop2h 58m

$168

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 1/14

9:45 am-1:10 pm

Nonstop2h 25m

Chicago Midway

Tue 1/20

8:10 am-10:00 am

Nonstop2h 50m

$176

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 2/7

8:20 am-11:45 am

Nonstop2h 25m

Chicago Midway

Mon 2/9

4:15 pm-5:55 pm

Nonstop2h 40m

$179

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 2/14

8:25 pm-11:45 pm

Nonstop2h 20m

Chicago Midway

Sun 2/15

2:05 pm-3:45 pm

Nonstop2h 40m

$179

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 1/24

3:15 pm-6:46 pm

Nonstop2h 31m

Chicago O'Hare Intl

Mon 1/26

2:36 pm-4:34 pm

Nonstop2h 58m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 53 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 December 19, 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 67 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, January is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $57). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $122). 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 December 23, 2025.

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 59% 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 December 16, 2024.

Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Tuesday mornings 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 December 23, 2025.

The most flights from BK9 to CHI are scheduled on a Monday (66 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (33 on average).

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

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 December 23, 2025.
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
4,253 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
9,106 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
11,050 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
5.8
Fair
3,074 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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 $147, Southwest can have you in Chicago from Breckenridge in 2h 25m. The distance from Breckenridge to Chicago is about 893 mi. This flight may include one or multiple stops.

  • 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: Volaris (100%), Royal Jordanian (88%), Copa Airlines( 87%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $926 for a flight from Breckenridge to Chicago. The cheapest flight overall is $64 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $124.

  • 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, January is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $57). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $122). 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

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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$173FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$156Average$278FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$375FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$162Average$395FlexibilityNo cancel feeOn-time69%

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