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$90+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Apr 24 — May 11
Fri 4/24
Fri 5/1
1 adult, Economy
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Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in August or September, 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 March 25, 2026.

This Southwest deal was found by Cheapflights users on 3/24. 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 5/1211:25 am
DEN
-
ORD
Nonstop2h 35m
Southwest
Wed 5/1311:55 am
ORD
-
DEN
2 stops8h 30m
Southwest
Deal found 3/24$174
This United Airlines deal was found by Cheapflights users on 3/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:20 pm
DEN
-
ORD
Nonstop2h 37m
United Airlines
Sat 5/98:20 pm
ORD
-
DEN
Nonstop2h 59m
United Airlines
Deal found 3/24$175
This Southwest deal was found by Cheapflights users on 3/24. 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.
Thu 4/168:20 pm
DEN
-
MDW
Nonstop2h 20m
Southwest
Tue 4/288:50 pm
MDW
-
DEN
Nonstop2h 45m
Southwest
Deal found 3/24$175
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 4/49:00 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Thu 4/95:15 am
ORD
-
DEN
1 stop7h 54m
Frontier
Deal found 3/24$176
This Southwest deal was found by Cheapflights users on 3/23. 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.
Sat 5/96:30 am
DEN
-
MDW
Nonstop2h 20m
Southwest
Tue 5/126:30 am
MDW
-
DEN
Nonstop2h 40m
Southwest
Deal found 3/23$176
This Super.com deal was found by Cheapflights users on 3/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:00 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Mon 4/132:29 pm
ORD
-
DEN
Nonstop3h 11m
Frontier
Deal found 3/22$177
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 4/812:13 am
DEN
-
ORD
1 stop11h 11m
Frontier
Sat 4/115:53 pm
ORD
-
DEN
Nonstop3h 08m
Frontier
Deal found 3/24$178
This Trip.com deal was found by Cheapflights users on 3/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:59 pm
DEN
-
MDW
1 stop15h 14m
Frontier
Sun 4/262:00 pm
MDW
-
DEN
1 stop19h 11m
Frontier
Deal found 3/24$178
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 4/812:13 am
DEN
-
ORD
1 stop11h 11m
Frontier
Sun 4/125:25 am
ORD
-
DEN
1 stop27h 45m
Frontier
Deal found 3/24$179
This Frontier deal was found by Cheapflights users on 3/21. 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 5/65:05 am
DEN
-
MDW
1 stop8h 07m
Frontier
Wed 5/1312:04 pm
MDW
-
DEN
1 stop11h 20m
Frontier
Deal found 3/21$179
This Expedia deal was found by Cheapflights users on 3/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:45 pm
DEN
-
ORD
1 stop6h 37m
Frontier
Mon 4/274:28 pm
ORD
-
DEN
1 stop7h 01m
Frontier
Deal found 3/20$180
This Frontier deal was found by Cheapflights users on 3/24. 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 5/295:05 am
DEN
-
MDW
1 stop8h 07m
Frontier
Sat 5/303:07 pm
MDW
-
DEN
1 stop9h 41m
Frontier
Deal found 3/24$180

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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$174
(Southwest)

One-way from

$90
(Cheapflightsfares)

Popular in

March

Cheapest in

August

Average price

$275
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. 8% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 25, 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 - ORD

DENORD

Denver Intl

Mon 6/8

7:10 pm-10:49 pm

Nonstop2h 39m

Chicago O'Hare Intl

Thu 6/11

10:55 pm-12:53 am

Nonstop2h 58m

$191

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 5/20

6:15 am-1:15 pm

1 stop6h 00m

Chicago O'Hare Intl

Mon 6/1

2:40 pm-11:45 pm

2 stops10h 05m

$200

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 5/5

2:50 pm-11:55 pm

1 stop8h 05m

Chicago O'Hare Intl

Thu 5/7

3:45 pm-11:45 pm

2 stops9h 00m

$201

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 4/22

6:15 am-1:15 pm

1 stop6h 00m

Chicago O'Hare Intl

Fri 4/24

6:15 pm-8:05 pm

Nonstop2h 50m

$201

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 5/30

8:35 am-2:20 pm

1 stop4h 45m

Chicago Midway

Mon 6/1

6:00 am-7:40 am

Nonstop2h 40m

$201

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 4/23

11:25 am-3:00 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 4/28

10:30 am-12:15 pm

Nonstop2h 45m

$202

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 4/21

11:45 am-4:40 pm

1 stop3h 55m

Chicago Midway

Sun 4/26

6:00 am-7:40 am

Nonstop2h 40m

$208

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 4/28

11:25 am-3:00 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 5/5

10:30 am-12:15 pm

Nonstop2h 45m

$217

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 4/16

6:05 am-3:30 pm

2 stops8h 25m

Chicago O'Hare Intl

Mon 4/20

4:15 pm-11:25 pm

2 stops8h 10m

$221

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 5/5

2:20 pm-7:50 pm

1 stop4h 30m

Chicago Midway

Tue 5/12

8:50 pm-10:35 pm

Nonstop2h 45m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 60 resultsSorted by cheapest first
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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 March 13, 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 month to book a flight from Breckenridge to Chicago?

Currently, April is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $81). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $140). 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 March 25, 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 62% 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 March 23, 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 March 25, 2026.

The most flights from BK9 to CHI are scheduled on a Tuesday (57 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 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 March 25, 2026.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
9,477 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
11,493 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
3,017 reviews
Southwest
8.0
Very good
4,333 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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 $191, United Airlines can have you in Chicago from Breckenridge in 2h 39m. The distance from Breckenridge to Chicago is about 886 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 $41 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 (82%), Cathay Pacific (80%), British Airways( 80%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $740 for a flight from Breckenridge to Chicago. The cheapest flight overall is $89 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $102.

  • 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, April is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $81). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $140). 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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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 March 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$75Average$186FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$126Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$155Average$296FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$157Average$386FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$162Average$396FlexibilityNo cancel feeOn-time69%

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