HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$62+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Breckenridge to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in October or February, booked 45 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 September 17, 2025.

Round-trip from

$116
(CheapOair)

One-way from

$62
(Cheapflightsfares)

Popular in

May

Cheapest in

October

Average price

$195
From Breckenridge to Chicago (CHI)
Search Deals
One-way flight from Breckenridge to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 10/228:22 pmDEN - ORD
Nonstop2h 31mFrontier
Sun 10/261:14 pmORD - DEN
1 stop19h 22mFrontier
Deal found 9/16$116
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Mon 10/2712:59 amDEN - MDW
1 stop9h 39mFrontier
Thu 10/3012:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/15$116
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/2212:59 amDEN - ORD
1 stop8h 42mFrontier
Sun 10/266:50 amORD - DEN
Nonstop2h 41mFrontier
Deal found 9/17$117
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Thu 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/96:30 amMDW - DEN
1 stop26h 06mFrontier
Deal found 9/15$117
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/15:50 pmDEN - ORD
Nonstop2h 38mFrontier
Sat 10/48:25 amORD - DEN
Nonstop2h 51mFrontier
Deal found 9/14$118
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Thu 10/239:12 pmDEN - MDW
Nonstop2h 24mFrontier
Sun 10/269:26 pmMDW - DEN
1 stop12h 37mFrontier
Deal found 9/16$118
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/2512:36 amDEN - ORD
1 stop29h 34mFrontier
Fri 10/316:00 amORD - DEN
Nonstop2h 41mFrontier
Deal found 9/14$119
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/129:12 pmDEN - MDW
Nonstop2h 24mFrontier
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/16$119
This Frontier deal was found by Cheapflights users on 9/15. 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 10/66:00 amDEN - ORD
Nonstop2h 37mFrontier
Wed 10/85:28 pmORD - DEN
1 stop7h 15mFrontier
Deal found 9/15$120
This CheapOair deal was found by Cheapflights users on 9/15. 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 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/1612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/15$120
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/179:19 pmDEN - ORD
Nonstop2h 40mFrontier
Sun 10/195:50 amORD - DEN
1 stop27h 53mFrontier
Deal found 9/15$121
This Frontier deal was found by Cheapflights users on 9/16. 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 11/1212:59 amDEN - ORD
1 stop8h 42mFrontier
Wed 11/197:20 amORD - DEN
Nonstop2h 49mFrontier
Deal found 9/16$122

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 September 17, 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

Sat 10/18

8:22 pm-11:53 pm

Nonstop2h 31m

Chicago O'Hare Intl

Mon 10/20

6:50 am-8:31 am

Nonstop2h 41m

$119

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 11/8

3:20 pm-6:53 pm

Nonstop2h 33m

Chicago O'Hare Intl

Sat 11/8

8:18 pm-10:07 pm

Nonstop2h 49m

$153

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 10/23

6:25 am-9:45 am

Nonstop2h 20m

Chicago Midway

Mon 10/27

6:25 pm-8:05 pm

Nonstop2h 40m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 1/17

3:15 pm-6:49 pm

Nonstop2h 34m

Chicago O'Hare Intl

Mon 1/19

7:00 am-8:49 am

Nonstop2h 49m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

7:15 pm-10:35 pm

Nonstop2h 20m

Chicago Midway

Mon 10/20

9:50 pm-11:25 pm

Nonstop2h 35m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 10/16

4:45 pm-8:25 pm

Nonstop2h 40m

Chicago O'Hare Intl

Mon 10/20

9:44 pm-11:30 pm

Nonstop2h 46m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 1/17

5:30 am-9:00 am

Nonstop2h 30m

Chicago Midway

Mon 1/19

5:40 am-7:30 am

Nonstop2h 50m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 10/8

6:40 am-2:25 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 10/8

6:55 pm-8:55 pm

Nonstop3h 00m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 10/15

7:20 pm-10:40 pm

Nonstop2h 20m

Chicago Midway

Wed 10/22

5:55 pm-10:05 pm

1 stop5h 10m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 11/3

10:15 am-5:00 pm

1 stop5h 45m

Chicago Midway

Wed 11/5

9:40 am-11:20 am

Nonstop2h 40m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 58 results
1
2
3
...
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 September 12, 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 45 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 September 17, 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 September 17, 2025.

The most flights from BK9 to CHI are scheduled on a Monday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 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 September 17, 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
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $157, Frontier can have you in Chicago from Breckenridge in 2h 20m. The distance from Breckenridge to Chicago is about 893 mi. All flights are typically nonstop.

  • 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 $69 on Frontier. Other airlines that offer cheap prices include United 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: Japan Airlines (85%), Cathay Pacific (85%), Turkish Airlines( 85%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $1,110 for a flight from Breckenridge to Chicago. The cheapest flight overall is $61 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $76.

  • 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
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Breckenridge to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Denver to O'Hare Intl flights
Denver to Midway flights
Denver to St. Louis flights
Denver to Moline flights
Colorado Springs to O'Hare Intl flights
Denver to Peoria flights
Montrose to O'Hare Intl flights
Aspen to O'Hare Intl flights
Denver to Bloomington flights
Durango to O'Hare Intl flights
Grand Junction to O'Hare Intl flights
Vail to O'Hare Intl flights
Colorado Springs to Midway flights
Hayden to O'Hare Intl flights
Colorado Springs to Evansville flights
Denver to Evansville flights
Denver to Rockford flights
Durango to St. Louis flights
Colorado Springs to St. Louis flights
Montrose to Midway flights
Denver to Springfield flights
Aspen to St. Louis flights
Denver to Decatur flights
Grand Junction to St. Louis flights
Grand Junction to Midway flights
Colorado Springs to Moline flights
Montrose to Peoria flights
Denver to Dubuque flights
Aspen to Midway flights
Montrose to St. Louis flights
Hayden to St. Louis flights
Grand Junction to Peoria flights
Denver to Champaign flights
Colorado Springs to Peoria flights
Colorado Springs to Bloomington flights
Vail to St. Louis flights
Grand Junction to Bloomington flights
Vail to Midway flights
Gunnison to O'Hare Intl flights
Gunnison to St. Louis flights
Colorado Springs to Champaign flights
Durango to Moline flights
Hayden to Moline flights
Durango to Midway flights
Colorado Springs to Springfield flights
Montrose to Springfield flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$165FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$152Average$295FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$165Average$424FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.