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$77+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
may. 17 — may. 241
sáb. 5/17
sáb. 5/24
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 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 mayo 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$141
(CheapOair)

One-way from

$77
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$208
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. 12% potential increase in price ($26 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 May 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 mayo 12, 2025.

This CheapOair deal was found by Cheapflights users on 5/11. 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.
vie. 7/118:21 pmDEN - ORD
Nonstop2h 38mFrontier
dom. 7/135:40 amORD - DEN
Nonstop2h 50mFrontier
Deal found 5/11$141
This CheapOair deal was found by Cheapflights users on 5/11. 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.
lun. 6/238:15 amDEN - MDW
Nonstop2h 25mFrontier
jue. 6/262:44 pmMDW - DEN
Nonstop2h 52mFrontier
Deal found 5/11$142
This American Airlines deal was found by Cheapflights users on 5/12. 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.
mié. 8/275:31 pmDEN - ORD
Nonstop2h 46mAmerican Airlines
sáb. 8/303:03 pmORD - DEN
Nonstop2h 38mAmerican Airlines
Deal found 5/12$160
This Southwest deal was found by Cheapflights users on 5/11. 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.
mié. 5/285:55 amDEN - MDW
Nonstop2h 25mSouthwest
mié. 7/25:15 amMDW - DEN
Nonstop2h 35mSouthwest
Deal found 5/11$165
This Booking.com deal was found by Cheapflights users on 5/11. 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.
jue. 6/1210:21 amDEN - ORD
1 stop7h 50mMultiple Airlines
sáb. 6/147:00 amORD - DEN
Nonstop2h 49mMultiple Airlines
Deal found 5/11$173
This Southwest deal was found by Cheapflights users on 5/12. 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.
jue. 8/285:20 amDEN - ORD
1 stop10h 05mSouthwest
mar. 9/97:00 amORD - DEN
Nonstop2h 40mSouthwest
Deal found 5/12$195
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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.
mié. 6/2510:23 amDEN - ORD
1 stop8h 24mSun Country Air
sáb. 6/286:10 amORD - DEN
1 stop10h 51mSun Country Air
Deal found 5/12$211
This Delta deal was found by Cheapflights users on 5/11. 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.
mar. 6/2412:55 amDEN - ORD
1 stop5h 54mDelta
mié. 7/23:54 pmORD - DEN
1 stop5h 34mDelta
Deal found 5/11$217
This Delta deal was found by Cheapflights users on 5/12. 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.
mié. 6/1112:55 amDEN - MDW
1 stop6h 46mDelta
sáb. 6/149:21 amMDW - DEN
1 stop7h 13mDelta
Deal found 5/12$217
This United Airlines deal was found by Cheapflights users on 5/12. 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.
dom. 5/257:50 amDEN - ORD
Nonstop2h 41mUnited Airlines
mié. 6/45:02 amORD - DEN
Nonstop2h 43mUnited Airlines
Deal found 5/12$234
This Mytrip deal was found by Cheapflights users on 5/12. 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.
vie. 7/258:00 amDEN - RFD
2 stops31h 27mAllegiant Air
dom. 7/2710:41 amRFD - DEN
2 stops31h 27mAllegiant Air
Deal found 5/12$360
This Mytrip deal was found by Cheapflights users on 5/12. 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.
vie. 7/184:05 pmDEN - RFD
2 stops15h 07mMultiple Airlines
dom. 7/209:21 amRFD - DEN
3 stops32h 58mMultiple Airlines
Deal found 5/12$418

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 mayo 12, 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

vie. 7/11

8:21 pm-11:59 pm

Nonstop2h 38m

Chicago O'Hare Intl

dom. 7/13

5:40 am-7:30 am

Nonstop2h 50m

$141

DenverChicago

DEN - MDW

DENMDW

Denver Intl

lun. 6/23

8:15 am-11:40 am

Nonstop2h 25m

Chicago Midway

jue. 6/26

2:44 pm-4:36 pm

Nonstop2h 52m

$142

DenverChicago

DEN - ORD

DENORD

Denver Intl

mié. 8/27

5:31 pm-9:17 pm

Nonstop2h 46m

Chicago O'Hare Intl

sáb. 8/30

3:03 pm-4:41 pm

Nonstop2h 38m

$160

DenverChicago

DEN - MDW

DENMDW

Denver Intl

mié. 5/28

5:55 am-9:20 am

Nonstop2h 25m

Chicago Midway

mié. 7/2

5:15 am-6:50 am

Nonstop2h 35m

$165

DenverChicago

DEN - ORD

DENORD

Denver Intl

jue. 6/12

10:21 am-7:11 pm

1 stop7h 50m

Chicago O'Hare Intl

sáb. 6/14

7:00 am-8:49 am

Nonstop2h 49m

$173

DenverChicago

DEN - ORD

DENORD

Denver Intl

mar. 6/3

7:30 pm-11:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

mar. 6/10

5:45 pm-10:40 pm

1 stop5h 55m

$179

DenverChicago

DEN - ORD

DENORD

Denver Intl

mié. 6/25

10:23 am-7:47 pm

1 stop8h 24m

Chicago O'Hare Intl

sáb. 6/28

6:10 am-4:01 pm

1 stop10h 51m

$211

DenverChicago

DEN - ORD

DENORD

Denver Intl

mar. 6/24

12:55 am-7:49 am

1 stop5h 54m

Chicago O'Hare Intl

sáb. 6/28

8:27 am-12:51 pm

1 stop5h 24m

$217

DenverChicago

DEN - MDW

DENMDW

Denver Intl

mié. 6/11

12:55 am-8:41 am

1 stop6h 46m

Chicago Midway

sáb. 6/14

9:21 am-3:34 pm

1 stop7h 13m

$217

DenverChicago

DEN - ORD

DENORD

Denver Intl

dom. 5/25

7:50 am-11:31 am

Nonstop2h 41m

Chicago O'Hare Intl

mié. 6/4

5:02 am-6:45 am

Nonstop2h 43m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 26 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 May 9, 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 mayo 12, 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. Sunday 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 mayo 12, 2025.

The most flights from BK9 to CHI are scheduled on a Monday (72 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (52 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 mayo 12, 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
10,000 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

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
4,290 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

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
8,724 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

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.
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

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 $77 on Frontier. Other airlines that offer cheap prices include Southwest from $81 and United Airlines from $85 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: Royal Jordanian (93%), Copa Airlines (92%), Japan Airlines( 91%).

  • What are the cheapest flights from Breckenridge to Chicago?

    On average you can expect to pay $983 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 $128.

  • 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

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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 mayo 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$143FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$151Average$374FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$155Average$293FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$155Average$426FlexibilityNo cancel feeOn-time69%

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