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$78+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in September or October, booked 30 days in advance, depart on a Friday or Thursday and return on a Friday

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 July 3, 2025.

Round-trip from

$149
(Priceline)

One-way from

$78
(Flightnetwork)

Popular in

May

Cheapest in

September

Average price

$205
From Breckenridge to Chicago (CHI)
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One-way flight from Breckenridge to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/208:31 pmDEN - ORD
Nonstop2h 39mFrontier
Thu 8/75:40 amORD - DEN
Nonstop2h 50mFrontier
Deal found 7/3$149
This Priceline deal was found by Cheapflights users on 7/2. 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.
Sat 8/2312:54 amDEN - MDW
1 stop8h 14mFrontier
Sat 8/306:10 amMDW - DEN
1 stop9h 08mFrontier
Deal found 7/2$153
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:20 amDEN - ORD
Nonstop2h 45mAmerican Airlines
Mon 12/1511:45 amORD - DEN
Nonstop2h 43mAmerican Airlines
Deal found 7/3$157
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/288:45 pmDEN - MDW
Nonstop2h 20mSouthwest
Sat 8/307:25 pmMDW - DEN
Nonstop2h 40mSouthwest
Deal found 7/2$157
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1610:25 amDEN - ORD
2 stops10h 05mSouthwest
Sat 9/207:00 amORD - DEN
Nonstop2h 40mSouthwest
Deal found 7/1$172
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:54 amDEN - RFD
2 stops22h 10mMultiple Airlines
Mon 10/133:07 pmRFD - DEN
2 stops20h 56mMultiple Airlines
Deal found 7/2$406
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/114:05 pmDEN - RFD
2 stops15h 07mAllegiant Air
Mon 7/148:42 amRFD - DEN
2 stops27h 51mAllegiant Air
Deal found 7/1$519

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 July 3, 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

Sun 7/20

8:31 pm-12:10 am

Nonstop2h 39m

Chicago O'Hare Intl

Thu 8/7

5:40 am-7:30 am

Nonstop2h 50m

$149

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 8/23

12:54 am-10:08 am

1 stop8h 14m

Chicago Midway

Sat 8/30

6:10 am-2:18 pm

1 stop9h 08m

$153

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 8/7

7:22 am-10:53 am

Nonstop2h 31m

Chicago O'Hare Intl

Mon 8/11

7:10 am-8:51 am

Nonstop2h 41m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 8/28

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Tue 9/2

8:50 pm-10:25 pm

Nonstop2h 35m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 9/16

10:25 am-9:30 pm

2 stops10h 05m

Chicago O'Hare Intl

Sat 9/20

7:00 am-8:40 am

Nonstop2h 40m

$172

DenverChicago

DEN - RFD

DENRFD

Denver Intl

Thu 7/31

5:42 pm-7:19 pm

2 stops24h 37m

Chicago Greater Rockford

Thu 8/7

9:21 am-7:43 am

2 stops23h 22m

$439

DenverChicago

DEN - RFD

DENRFD

Denver Intl

Fri 7/11

4:05 pm-8:12 am

2 stops15h 07m

Chicago Greater Rockford

Mon 7/14

8:42 am-11:33 am

2 stops27h 51m

$519

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 8/14

8:53 pm-12:32 am

Nonstop2h 39m

$78

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 8/14

5:26 pm-8:54 pm

Nonstop2h 28m

$78

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 8/19

8:28 pm-11:59 pm

Nonstop2h 31m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 17 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 June 27, 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 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 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 July 3, 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 July 3, 2025.

The most flights from BK9 to CHI are scheduled on a Thursday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 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 July 3, 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
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 cheapest airlines to fly from Breckenridge to Chicago one-way?

    One-way options have recently been found by users for as low as $78 on Frontier. Other airlines that offer cheap prices include American Airlines from $79 and Southwest from $79 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: Turkish Airlines (97%), Copa Airlines (96%), Brussels Airlines( 89%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $2,030 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 $97.

  • 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 Breckenridge?

Book flights to Breckenridge if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$155FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$151Average$352FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$155Average$293FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$159Average$429FlexibilityNo cancel feeOn-time69%

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