$79+ Cheap flights from Chicago (CHI) to Breckenridge, CO
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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Chicago to Breckenridge 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 Chicago to Breckenridge are usually found in October or September, booked 71 days in advance, depart on a Saturday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Breckenridge
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Cheapest flights from Chicago to BreckenridgeExplore the most affordable flight options available from Chicago to Breckenridge. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Chicago to Breckenridge. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:29 pm
ORD
- DEN
Nonstop3h 11m
Frontier
Mon 4/134:08 pm
DEN
- ORD
1 stop13h 39m
Frontier
Deal found 2/1![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:30 am
ORD
- DEN
1 stop13h 19m
Frontier
Sun 3/86:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Deal found 2/2![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Mon 5/187:05 pm
DEN
- ORD
1 stop10h 42m
Frontier
Deal found 2/2![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:16 pm
MDW
- DEN
1 stop9h 46m
Frontier
Tue 3/106:01 pm
DEN
- MDW
1 stop15h 24m
Frontier
Deal found 2/2![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:16 pm
ORD
- DEN
2 stops26h 19m
Multiple Airlines
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:16 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Sat 2/284:10 pm
DEN
- ORD
1 stop6h 07m
Frontier
Deal found 2/1![Frontier logo]()
$124
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/54:16 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 2/3![Frontier logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:51 am
ORD
- DEN
1 stop10h 44m
Frontier
Fri 2/279:41 am
DEN
- ORD
Nonstop2h 44m
Frontier
Deal found 2/3![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:51 am
ORD
- DEN
1 stop10h 50m
Frontier
Tue 3/312:59 am
DEN
- ORD
1 stop8h 52m
Frontier
Deal found 2/1![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:16 pm
ORD
- DEN
2 stops17h 53m
Multiple Airlines
Thu 3/57:35 pm
DEN
- ORD
Nonstop2h 39m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:05 am
ORD
- DEN
1 stop11h 39m
Frontier
Fri 3/69:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 2/3![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
- DEN
1 stop15h 20m
Frontier
Sat 3/79:30 pm
DEN
- MDW
1 stop22h 22m
Frontier
Deal found 2/2![Frontier logo]()
$133
Best flights from Chicago to BreckenridgeDiscover carefully curated flight deals from Chicago to Breckenridge that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Chicago to Breckenridge that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Southwest deal was found by Cheapflights users on 1/31. 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 4/186:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Thu 4/238:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 1/31![Southwest logo]()
$175
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:35 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Mon 4/137:17 pm
DEN
- ORD
Nonstop2h 37m
United Airlines
Deal found 2/2![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sat 4/47:20 pm
ORD
- DEN
1 stop6h 55m
Southwest
Sat 4/118:20 am
DEN
- ORD
1 stop6h 10m
Southwest
Deal found 2/1![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:50 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Tue 3/173:10 pm
DEN
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/1![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 4/15:55 am
MDW
- DEN
Nonstop2h 45m
Southwest
Sat 4/45:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 2/2![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/282:02 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Tue 3/38:30 pm
DEN
- ORD
Nonstop2h 29m
United Airlines
Deal found 2/2![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 2/258:10 am
MDW
- DEN
Nonstop2h 50m
Southwest
Wed 3/44:35 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 2/1![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:03 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Sun 4/128:52 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/2![United Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 3/184:50 pm
ORD
- DEN
Nonstop2h 45m
Southwest
Wed 3/2510:10 am
DEN
- ORD
Nonstop2h 45m
Southwest
Deal found 2/1![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Mon 4/69:40 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Thu 4/98:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 2/2![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Mon 3/309:40 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Fri 4/36:20 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 2/2![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 4/103:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 4/138:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 2/2![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 4/109:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Tue 4/1410:55 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 2/2![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 3/1110:05 am
MDW
- DEN
Nonstop2h 45m
Southwest
Wed 3/188:10 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 2/2![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 3/76:20 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Tue 3/101:25 pm
DEN
- MDW
Nonstop2h 15m
Southwest
Deal found 2/2![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 4/2910:20 am
MDW
- DEN
1 stop4h 50m
Southwest
Wed 5/65:55 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Deal found 2/2![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 4/2910:30 am
ORD
- DEN
Nonstop2h 45m
Southwest
Wed 5/62:50 pm
DEN
- ORD
1 stop8h 05m
Southwest
Deal found 2/2![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 2/1. 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.
Mon 4/65:40 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Wed 4/85:55 am
DEN
- MDW
1 stop4h 40m
Southwest
Deal found 2/1![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 2/1. 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 3/31:45 pm
ORD
- DEN
1 stop6h 35m
Southwest
Tue 3/1010:10 am
DEN
- ORD
Nonstop2h 45m
Southwest
Deal found 2/1![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:45 pm
ORD
- DEN
1 stop6h 35m
Southwest
Thu 3/511:30 am
DEN
- ORD
Nonstop2h 35m
Southwest
Deal found 2/3![Southwest logo]()
$208
Last-minute flights from Chicago to BreckenridgeDiscover last-minute flight deals from Chicago to Breckenridge. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Breckenridge. Data last updated February 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:30 am
ORD
- DEN
1 stop15h 29m
Frontier
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 2/1![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:51 am
ORD
- DEN
1 stop10h 50m
Frontier
Tue 3/312:59 am
DEN
- ORD
1 stop8h 52m
Frontier
Deal found 2/1![Frontier logo]()
$128
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:51 am
ORD
- DEN
1 stop10h 44m
Frontier
Fri 2/279:41 am
DEN
- ORD
Nonstop2h 44m
Frontier
Deal found 2/3![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:16 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Sat 2/284:10 pm
DEN
- ORD
1 stop6h 07m
Frontier
Deal found 2/1![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:16 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Tue 3/312:59 am
DEN
- ORD
1 stop8h 52m
Frontier
Deal found 2/1![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:30 am
ORD
- DEN
1 stop13h 19m
Frontier
Sun 3/86:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Deal found 2/2![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:05 am
ORD
- DEN
1 stop11h 39m
Frontier
Fri 3/69:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 2/3![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:05 am
ORD
- DEN
1 stop11h 39m
Frontier
Mon 3/212:59 am
DEN
- ORD
1 stop8h 52m
Frontier
Deal found 2/2![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:16 pm
ORD
- DEN
2 stops26h 19m
Multiple Airlines
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:16 pm
ORD
- DEN
2 stops17h 53m
Multiple Airlines
Thu 3/57:35 pm
DEN
- ORD
Nonstop2h 39m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/54:16 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 2/3![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:16 pm
MDW
- DEN
1 stop9h 46m
Frontier
Tue 3/106:01 pm
DEN
- MDW
1 stop15h 24m
Frontier
Deal found 2/2![Frontier logo]()
$123
One-way flights from Chicago to BreckenridgeSearch for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:05 am
MDW
- DEN
1 stop7h 04m
Frontier
Deal found 2/3![Frontier logo]()
$79
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/211:37 pm
ORD
- DEN
1 stop9h 12m
Frontier
Deal found 2/3![Frontier logo]()
$79
This Frontier deal was found by Cheapflights users on 2/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- DEN
1 stop7h 38m
Frontier
Deal found 2/3![Frontier logo]()
$80
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
ORD
- DEN
1 stop26h 20m
Frontier
Deal found 2/3![Frontier logo]()
$80
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 2/283:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/2![Southwest logo]()
$81
This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 5/23:05 pm
ORD
- DEN
Nonstop3h 00m
Southwest
Deal found 2/2![Southwest logo]()
$81
This Trip.com deal was found by Cheapflights users on 2/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:09 pm
MDW
- DEN
1 stop7h 42m
Frontier
Deal found 2/3![Frontier logo]()
$83
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:53 pm
ORD
- DEN
Nonstop2h 58m
Frontier
Deal found 2/3![Frontier logo]()
$83
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:16 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Deal found 2/3![Frontier logo]()
$84
This Priceline deal was found by Cheapflights users on 2/3. 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.
Thu 4/92:56 pm
MDW
- DEN
1 stop9h 08m
Frontier
Deal found 2/3![Frontier logo]()
$85
This Priceline deal was found by Cheapflights users on 2/3. 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.
Thu 2/193:00 pm
MDW
- DEN
1 stop9h 17m
Frontier
Deal found 2/3![Frontier logo]()
$86
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:32 am
ORD
- DEN
1 stop14h 36m
Frontier
Deal found 2/3![Frontier logo]()
$86
Find flight deals from Chicago to Breckenridge
Keep the following information in mind while searching for Chicago to Breckenridge flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $120 (Cheapflightsfares) |
One-way from | $79 (Super.com) |
Popular in | December |
Cheapest in | October |
Average price | $203 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Breckenridge 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 February 3, 2026.
Use the filters below to find and compare flights from Chicago to Breckenridge that are best for you.
Fly from
Chicago
Fly to
Breckenridge
Route
Depart
Return
Price
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Sat 4/18
6:00 am-7:40 am
Nonstop2h 40m
Denver Intl
Thu 4/23
8:20 pm-11:40 pm
Nonstop2h 20m
$175
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Sat 4/4
7:20 pm-1:15 am
1 stop6h 55m
Denver Intl
Sat 4/11
8:20 am-3:30 pm
1 stop6h 10m
$179
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 4/1
5:55 am-7:40 am
Nonstop2h 45m
Denver Intl
Sat 4/4
5:55 am-9:20 am
Nonstop2h 25m
$188
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 2/25
8:10 am-10:00 am
Nonstop2h 50m
Denver Intl
Wed 3/4
4:35 pm-7:55 pm
Nonstop2h 20m
$189
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Fri 4/10
2:35 pm-4:29 pm
Nonstop2h 54m
Denver Intl
Mon 4/13
7:17 pm-10:54 pm
Nonstop2h 37m
$191
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Thu 3/12
12:50 pm-2:48 pm
Nonstop2h 58m
Denver Intl
Tue 3/17
3:10 pm-6:45 pm
Nonstop2h 35m
$191
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Wed 3/18
4:50 pm-6:35 pm
Nonstop2h 45m
Denver Intl
Wed 3/25
10:10 am-1:55 pm
Nonstop2h 45m
$191
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Mon 4/6
9:40 pm-11:20 pm
Nonstop2h 40m
Denver Intl
Thu 4/9
8:20 pm-11:40 pm
Nonstop2h 20m
$191
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Mon 3/30
9:40 pm-11:20 pm
Nonstop2h 40m
Denver Intl
Fri 4/3
6:20 am-9:45 am
Nonstop2h 25m
$191
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 4/10
3:30 pm-5:10 pm
Nonstop2h 40m
Denver Intl
Mon 4/13
8:20 pm-11:40 pm
Nonstop2h 20m
$191
Showing 1-10 of 41 results
Best time to book a flight from Chicago to Breckenridge
Have a flexible travel schedule? Discover the best time to fly to Breckenridge from Chicago with our price prediction graph.
MDW-DEN
ORD-DEN
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 Chicago to Breckenridge
CHI-BK9
MDW-DEN
ORD-DEN
How far ahead should I book a flight from Chicago to Breckenridge?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Breckenridge. Price data was last updated on January 30, 2026.
The price you pay for your flight from Chicago to Breckenridge may vary depending on when you book. For the best chance of a lower fare, look to book 71 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 Chicago to Breckenridge?
Currently, March is the cheapest month in which you can book a flight from Chicago to Breckenridge (average of $55). Flying from Chicago to Breckenridge in July is currently the most expensive (average of $115). 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 CHI to BK9?
Find hourly flight availability from Chicago to Breckenridge. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 3, 2026.
It’s typically best to fly out from Chicago to Breckenridge in the afternoon. Doing so could potentially save you 13% on the flight price compared to flying in the evening, which is usually more expensive.
What is the cheapest day to fly from Chicago to Breckenridge?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Breckenridge. Price data was last updated on January 31, 2026.
Travelers seeking maximum savings on their Chicago to Breckenridge flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Breckenridge
Explore weekly flight availability from Chicago to Breckenridge. 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 February 3, 2026.
The most flights from CHI to BK9 are scheduled on a Tuesday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Chicago to Breckenridge?
Reviews of airlines servicing Breckenridge
Get insights into the airlines that provide service to Breckenridge. 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 Breckenridge. Reviews last updated February 3, 2026.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Breckenridge have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Breckenridge. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Breckenridge
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Complete your trip
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Chicago and Breckenridge flights
Browse other Chicago and Breckenridge flight options. Last updated on February 3, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Breckenridge flights
Consider these flights traveling from Chicago to Breckenridge.
Top 5 airlines flying from Chicago to Breckenridge
Discover the top 5 airlines that operate flights from Chicago to Breckenridge. 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$163 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$154 | Average$337 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$155 | Average$410 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$298 | FlexibilityNo cancel fee | On-time63% |