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$87+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in August or January, booked 79 days in advance, depart on a Thursday or Friday and return on a Saturday

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 April 23, 2026.

This Frontier deal was found by Cheapflights users on 4/19. 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.
Tue 5/2611:54 pm
DEN
-
ORD
1 stop7h 01m
Frontier
Thu 5/284:05 pm
ORD
-
DEN
1 stop8h 53m
Frontier
Deal found 4/19$185
This Priceline deal was found by Cheapflights users on 4/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:54 pm
DEN
-
MDW
1 stop10h 15m
Frontier
Tue 5/2612:27 pm
MDW
-
DEN
1 stop10h 57m
Frontier
Deal found 4/21$185
This Super.com deal was found by Cheapflights users on 4/19. 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.
Wed 5/65:05 am
DEN
-
MDW
1 stop8h 07m
Frontier
Fri 5/84:52 pm
MDW
-
DEN
1 stop16h 32m
Frontier
Deal found 4/19$186
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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.
Sat 6/2711:46 pm
DEN
-
ORD
1 stop7h 17m
Frontier
Wed 7/19:48 pm
ORD
-
DEN
Nonstop3h 06m
Frontier
Deal found 4/19$187
This Super.com deal was found by Cheapflights users on 4/21. 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.
Sat 5/234:54 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Sun 5/249:37 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Deal found 4/21$188
This Booking.com deal was found by Cheapflights users on 4/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:05 am
DEN
-
MDW
1 stop8h 07m
Frontier
Mon 5/184:52 pm
MDW
-
DEN
1 stop31h 19m
Frontier
Deal found 4/20$188
This Frontier deal was found by Cheapflights users on 4/21. 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.
Thu 5/214:54 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Sat 5/309:37 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Deal found 4/21$189
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:05 am
DEN
-
MDW
1 stop4h 30m
Southwest
Tue 5/266:30 am
MDW
-
DEN
Nonstop2h 40m
Southwest
Deal found 4/21$189
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:05 am
DEN
-
ORD
2 stops8h 00m
Multiple Airlines
Fri 5/299:37 pm
ORD
-
DEN
Nonstop3h 07m
Multiple Airlines
Deal found 4/21$190
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:05 am
DEN
-
ORD
2 stops8h 00m
Multiple Airlines
Wed 5/279:37 pm
ORD
-
DEN
Nonstop3h 07m
Multiple Airlines
Deal found 4/20$191
This Super.com deal was found by Cheapflights users on 4/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:54 pm
DEN
-
MDW
1 stop10h 15m
Frontier
Fri 5/84:52 pm
MDW
-
DEN
1 stop16h 32m
Frontier
Deal found 4/18$191
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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 5/2111:54 pm
DEN
-
ORD
1 stop7h 01m
Frontier
Sat 5/239:37 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Deal found 4/19$192

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$185
(Frontier)

One-way from

$87
(Super.com)

Popular in

March

Cheapest in

August

Average price

$279
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. 13% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 23, 2026.
Use the filters below to find and compare flights from Breckenridge to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/28

8:20 pm-11:40 pm

Nonstop2h 20m

Chicago Midway

Mon 6/1

9:35 pm-11:15 pm

Nonstop2h 40m

$207

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/28

6:35 am-9:55 am

Nonstop2h 20m

Chicago Midway

Thu 5/28

9:35 pm-11:15 pm

Nonstop2h 40m

$214

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 8/12

10:45 am-8:17 pm

1 stop8h 32m

Chicago O'Hare Intl

Fri 8/14

3:50 pm-10:29 pm

1 stop7h 39m

$229

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 8/25

12:55 am-8:42 am

1 stop6h 47m

Chicago Midway

Fri 8/28

5:25 pm-11:45 pm

1 stop7h 20m

$253

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 6/9

6:00 pm-9:39 pm

Nonstop2h 39m

Chicago O'Hare Intl

Sat 6/13

5:00 am-6:38 am

Nonstop2h 38m

$255

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 6/23

10:15 am-4:55 pm

1 stop5h 40m

Chicago Midway

Wed 7/1

7:00 am-8:35 am

Nonstop2h 35m

$255
Quickest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 8/14

7:00 am-10:20 am

Nonstop2h 20m

Chicago Midway

Sun 8/16

6:30 am-8:00 am

Nonstop2h 30m

$263

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 10/1

8:34 pm-11:57 pm

Nonstop2h 23m

Chicago O'Hare Intl

Sun 10/4

5:00 am-6:42 am

Nonstop2h 42m

$265

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 5/9

10:48 am-5:56 pm

1 stop6h 08m

Chicago Midway

Wed 5/13

9:22 am-1:59 pm

1 stop5h 37m

$267

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 6/3

12:55 am-8:43 am

1 stop6h 48m

Chicago Midway

Tue 6/9

9:54 am-3:40 pm

1 stop6h 46m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 April 17, 2026.

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 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 April 23, 2026.

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 57% 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 April 18, 2026.

Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Saturday afternoons 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 April 23, 2026.

The most flights from BK9 to CHI are scheduled on a Thursday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 April 23, 2026.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,635 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,952 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,659 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,981 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $207, Southwest can have you in Chicago from Breckenridge in 2h 20m. 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: Copa Airlines (85%), Envoy Air (79%), Aer Lingus( 78%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $754 for a flight from Breckenridge to Chicago. The cheapest flight overall is $84 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $101.

  • 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 5 airlines flying from Breckenridge to Chicago

Discover the top 5 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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$188FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$126Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$303FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$159Average$388FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$167Average$403FlexibilityNo cancel feeOn-time69%

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