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$76+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheapflights Tip: The best prices from Breckenridge to Chicago are usually found in September or October, booked 84 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 April 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$141
(Cheapflightsfares)

One-way from

$76
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$196
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
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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. 8% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 7/38:21 pmDEN - ORD
Nonstop2h 38mFrontier
Sat 7/57:00 amORD - DEN
Nonstop2h 53mFrontier
Deal found 4/28$129
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 6/119:30 pmDEN - MDW
Nonstop2h 25mSouthwest
Wed 7/165:15 amMDW - DEN
Nonstop2h 35mSouthwest
Deal found 4/28$151
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 6/208:15 amDEN - MDW
Nonstop2h 25mFrontier
Mon 6/2312:35 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 4/29$152
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 9/45:32 pmDEN - ORD
Nonstop2h 50mAmerican Airlines
Sun 9/76:48 amORD - DEN
Nonstop2h 34mAmerican Airlines
Deal found 4/29$160
This Southwest deal was found by Cheapflights users on 4/28. 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 5/247:30 pmDEN - ORD
Nonstop2h 35mSouthwest
Sun 5/2512:40 pmORD - DEN
Nonstop2h 45mSouthwest
Deal found 4/28$165
This Booking.com deal was found by Cheapflights users on 4/29. 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.
Mon 8/1110:14 amDEN - ORD
1 stop7h 57mMultiple Airlines
Fri 8/155:40 amORD - DEN
Nonstop2h 50mMultiple Airlines
Deal found 4/29$168
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/1212:59 amDEN - ORD
1 stop6h 40mDelta
Fri 6/205:15 pmORD - DEN
1 stop6h 43mDelta
Deal found 4/29$217
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/126:20 amDEN - MDW
1 stop5h 09mDelta
Tue 6/177:21 pmMDW - DEN
1 stop5h 01mDelta
Deal found 4/29$217
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 6/48:50 pmDEN - ORD
Nonstop2h 35mUnited Airlines
Mon 6/99:40 pmORD - DEN
Nonstop2h 50mUnited Airlines
Deal found 4/28$220
This Sun Country Air deal was found by Cheapflights users on 4/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:11 amDEN - ORD
1 stop8h 01mSun Country Air
Mon 9/2911:47 amORD - DEN
1 stop5h 47mSun Country Air
Deal found 4/29$245
This Mytrip deal was found by Cheapflights users on 4/29. 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 5/225:50 pmDEN - RFD
2 stops24h 22mAllegiant Air
Sat 5/248:46 amRFD - DEN
2 stops25h 15mAllegiant Air
Deal found 4/29$460

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 29, 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

Tue 7/1

8:05 pm-11:43 pm

Nonstop2h 38m

Chicago O'Hare Intl

Wed 7/2

7:00 am-8:49 am

Nonstop2h 49m

$141

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 5/27

7:30 pm-11:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 6/3

7:00 am-8:40 am

Nonstop2h 40m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 6/11

9:30 pm-12:55 am

Nonstop2h 25m

Chicago Midway

Wed 7/16

5:15 am-6:50 am

Nonstop2h 35m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 6/20

8:15 am-11:40 am

Nonstop2h 25m

Chicago Midway

Mon 6/23

12:35 pm-2:23 pm

Nonstop2h 48m

$152

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 9/4

5:32 pm-9:22 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 9/7

6:48 am-8:22 am

Nonstop2h 34m

$160

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sun 6/29

6:15 am-7:17 pm

1 stop12h 02m

Chicago O'Hare Intl

Wed 7/9

7:00 am-8:53 am

Nonstop2h 53m

$168

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 5/21

8:57 pm-12:29 am

Nonstop2h 32m

Chicago O'Hare Intl

Sat 5/24

1:15 pm-2:57 pm

Nonstop2h 42m

$211

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 6/12

12:59 am-8:39 am

1 stop6h 40m

Chicago O'Hare Intl

Fri 6/20

5:59 pm-12:21 am

1 stop7h 22m

$217

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 6/12

9:21 am-5:40 pm

1 stop7h 19m

Chicago Midway

Thu 6/19

6:47 pm-12:21 am

1 stop6h 34m

$217

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 8/28

6:07 pm-11:32 am

1 stop16h 25m

Chicago O'Hare Intl

Fri 9/12

12:01 pm-5:31 pm

1 stop6h 30m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 27 results
1
2
3

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 25, 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 84 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 April 29, 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 Wednesday 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 April 29, 2025.

The most flights from BK9 to CHI are scheduled on a Tuesday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 29, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Breckenridge to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $76 on United Airlines. Other airlines that offer cheap prices include Southwest from $76 and Frontier 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: Copa Airlines (90%), Royal Jordanian (88%), Cathay Pacific( 87%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $1,158 for a flight from Breckenridge to Chicago. The cheapest flight overall is $79 while the most popular route, (Denver Intl - Chicago O'Hare Intl) is currently priced at $116.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$139FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$150Average$403FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$154Average$431FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$155Average$292FlexibilityNo cancel feeOn-time63%

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