$82+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Apr 5 — Apr 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 March 6, 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 March 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Tue 4/2111:59 pm
DEN
- ORD
1 stop9h 03m
Frontier
Deal found 3/1![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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 5/810:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Mon 5/111:09 pm
DEN
- ORD
1 stop8h 30m
Frontier
Deal found 3/1![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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 4/139:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Sat 4/115:53 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/203:45 pm
DEN
- ORD
1 stop6h 21m
Frontier
Deal found 3/1![Frontier logo]()
$116
This Expedia deal was found by Cheapflights users on 3/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:53 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/1310:30 pm
DEN
- ORD
1 stop6h 50m
Frontier
Deal found 3/1![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/209:00 pm
DEN
- ORD
1 stop16h 07m
Frontier
Deal found 3/1![Frontier logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Thu 4/308:58 pm
ORD
- DEN
1 stop8h 01m
Frontier
Sun 5/36:10 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/1![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Sat 4/45:53 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Wed 4/810:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Fri 5/16:09 pm
ORD
- DEN
1 stop6h 35m
Frontier
Sun 5/36:10 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/1![Frontier logo]()
$123
This Expedia deal was found by Cheapflights users on 3/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:11 am
ORD
- DEN
1 stop12h 42m
Frontier
Sun 4/196:10 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/1![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 3/1. 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.
Fri 4/1011:55 am
ORD
- DEN
1 stop9h 54m
Frontier
Sat 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/1![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Thu 5/74:09 pm
MDW
- DEN
1 stop7h 42m
Frontier
Tue 5/1211:59 pm
DEN
- MDW
1 stop18h 32m
Frontier
Deal found 3/2![Frontier logo]()
$135
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 March 6, 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 March 6, 2026.
This Southwest deal was found by Cheapflights users on 3/3. 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 4/2810:30 am
ORD
- DEN
Nonstop2h 45m
Southwest
Tue 5/1211:25 am
DEN
- ORD
Nonstop2h 35m
Southwest
Deal found 3/3![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Wed 4/17:00 am
ORD
- DEN
Nonstop2h 55m
United Airlines
Wed 4/18:52 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Deal found 3/1![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:35 am
ORD
- DEN
1 stop7h 56m
Delta
Thu 7/92:20 pm
DEN
- ORD
1 stop4h 23m
Delta
Deal found 3/1![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 3/4. 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 4/45:55 am
MDW
- DEN
Nonstop2h 45m
Southwest
Tue 4/76:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/4![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Wed 5/2011:05 am
DEN
- MDW
1 stop4h 30m
Southwest
Deal found 3/5![Southwest logo]()
$195
This United Airlines deal was found by Cheapflights users on 3/2. 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.
Tue 5/197:10 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Tue 5/264:45 pm
DEN
- ORD
Nonstop2h 45m
United Airlines
Deal found 3/2![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 3/4. 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 5/136:30 am
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/186:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/4![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:05 pm
ORD
- DEN
1 stop4h 36m
Delta
Fri 6/510:48 am
DEN
- ORD
1 stop7h 32m
Delta
Deal found 3/1![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 3/2. 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 4/110:10 am
MDW
- DEN
1 stop5h 15m
Southwest
Wed 4/16:10 pm
DEN
- MDW
1 stop4h 55m
Southwest
Deal found 3/2![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/1. 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.
Fri 5/85:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/116:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/1![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Tue 4/146:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/5![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/211:40 am
MDW
- DEN
1 stop6h 10m
Southwest
Tue 4/78:40 am
DEN
- MDW
2 stops5h 15m
Southwest
Deal found 3/5![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 3/3. 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 4/710:30 am
ORD
- DEN
Nonstop2h 45m
Southwest
Fri 4/105:20 am
DEN
- ORD
1 stop6h 30m
Southwest
Deal found 3/3![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/5. 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 5/83:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Sun 5/105:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 3/5![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/3. 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 4/75:30 am
MDW
- DEN
1 stop5h 40m
Southwest
Fri 4/106:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/3![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/2. 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 6/245:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Sun 6/285:50 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 3/2![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 3/6. 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 4/202:40 pm
ORD
- DEN
2 stops10h 05m
Southwest
Mon 4/273:00 pm
DEN
- ORD
1 stop7h 55m
Southwest
Deal found 3/6![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 3/3. 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.
Sun 5/36:30 am
MDW
- DEN
1 stop4h 20m
Southwest
Sun 5/175:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 3/3![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/5. 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 4/173:45 pm
ORD
- DEN
2 stops9h 00m
Southwest
Mon 4/205:20 am
DEN
- ORD
1 stop6h 30m
Southwest
Deal found 3/5![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 3/1. 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 6/305:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Tue 7/78:30 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/1![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 3/5. 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 4/172:40 pm
ORD
- DEN
2 stops9h 20m
Southwest
Sun 4/196:10 am
DEN
- ORD
1 stop8h 20m
Southwest
Deal found 3/5![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 3/1. 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 5/277:45 am
ORD
- DEN
2 stops10h 45m
Southwest
Fri 5/294:00 pm
DEN
- ORD
1 stop6h 55m
Southwest
Deal found 3/1![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:40 pm
ORD
- DEN
2 stops9h 20m
Southwest
Sun 5/109:15 am
DEN
- ORD
1 stop8h 35m
Southwest
Deal found 3/5![Southwest logo]()
$280
Last-minute flights from Chicago to BreckenridgeDiscover last-minute flight deals from Chicago to Breckenridge. Data last updated March 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Breckenridge. Data last updated March 6, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Tue 4/2111:59 pm
DEN
- ORD
1 stop9h 03m
Frontier
Deal found 3/1![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/209:00 pm
DEN
- ORD
1 stop16h 07m
Frontier
Deal found 3/1![Frontier logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Sat 4/45:53 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Wed 4/810:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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 4/139:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 3/1![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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 4/107:40 am
ORD
- DEN
1 stop17h 28m
Frontier
Sat 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/1![Frontier logo]()
$123
This Lucky2Go deal was found by Cheapflights users on 3/1. 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 Lucky2Go 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
Sun 4/1211:59 pm
DEN
- ORD
1 stop22h 37m
Frontier
Deal found 3/1![Frontier logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Sat 4/115:53 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/203:45 pm
DEN
- ORD
1 stop6h 21m
Frontier
Deal found 3/1![Frontier logo]()
$116
This Expedia deal was found by Cheapflights users on 3/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:53 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/1310:30 pm
DEN
- ORD
1 stop6h 50m
Frontier
Deal found 3/1![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/152:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Thu 5/76:30 am
DEN
- MDW
1 stop7h 19m
Frontier
Deal found 3/5![Frontier logo]()
$136
This Frontier deal was found by Cheapflights users on 3/1. 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.
Fri 4/178:58 pm
ORD
- DEN
1 stop8h 01m
Frontier
Mon 4/206:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/1![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Mon 4/202:15 pm
MDW
- DEN
1 stop22h 59m
Frontier
Mon 4/271:07 pm
DEN
- MDW
1 stop8h 12m
Frontier
Deal found 3/6![Frontier logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Thu 4/308:58 pm
ORD
- DEN
1 stop8h 01m
Frontier
Sun 5/36:10 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/1![Frontier logo]()
$121
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 March 6, 2026.
Search for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated March 6, 2026.
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Sat 5/95:45 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 3/1![United Airlines logo]()
$82
This Trip.com deal was found by Cheapflights users on 3/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/1![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 3/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 3/1![Frontier logo]()
$83
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 5/1410:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 3/3![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 3/3. 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 4/116:40 am
MDW
- DEN
1 stop11h 18m
Frontier
Deal found 3/3![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 3/3. 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.
Sun 5/175:25 am
ORD
- DEN
1 stop28h 03m
Frontier
Deal found 3/3![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 3/4. 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.
Mon 4/65:11 pm
MDW
- DEN
1 stop20h 56m
Frontier
Deal found 3/4![Frontier logo]()
$85
This Cheapflightsfares deal was found by Cheapflights users on 3/6. 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 3/6![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 3/176:00 am
MDW
- DEN
1 stop18h 04m
Frontier
Deal found 3/6![Frontier logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 3/6. 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.
Mon 5/1810:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 3/6![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 3/5. 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.
Fri 4/179:14 am
MDW
- DEN
1 stop14h 45m
Frontier
Deal found 3/5![Frontier logo]()
$88
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:05 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 3/3![United Airlines logo]()
$89
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 March 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $113 (Kiwi.com) |
One-way from | $82 (United Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $226 |
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 March 6, 2026.
Use the filters below to find and compare flights from Chicago to Breckenridge that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Tue 4/28
10:30 am-12:15 pm
Nonstop2h 45m
Denver Intl
Tue 5/12
11:25 am-3:00 pm
Nonstop2h 35m
$177
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Sat 4/4
5:55 am-7:40 am
Nonstop2h 45m
Denver Intl
Tue 4/7
6:35 am-9:55 am
Nonstop2h 20m
$186
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Thu 5/14
6:00 am-7:40 am
Nonstop2h 40m
Denver Intl
Wed 5/20
11:05 am-4:35 pm
1 stop4h 30m
$195
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Wed 4/1
7:00 am-8:55 am
Nonstop2h 55m
Denver Intl
Wed 4/1
8:52 pm-12:30 am
Nonstop2h 38m
$197
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 5/13
6:30 am-8:10 am
Nonstop2h 40m
Denver Intl
Mon 5/18
6:35 am-9:55 am
Nonstop2h 20m
$197
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 4/1
10:10 am-2:25 pm
1 stop5h 15m
Denver Intl
Wed 4/1
6:10 pm-12:05 am
1 stop4h 55m
$197
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 5/8
5:15 pm-6:55 pm
Nonstop2h 40m
Denver Intl
Mon 5/11
6:35 am-9:55 am
Nonstop2h 20m
$197
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Thu 4/9
3:30 pm-5:10 pm
Nonstop2h 40m
Denver Intl
Tue 4/14
6:35 am-9:55 am
Nonstop2h 20m
$201
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Thu 4/2
11:40 am-4:50 pm
1 stop6h 10m
Denver Intl
Tue 4/7
8:40 am-2:55 pm
2 stops5h 15m
$214
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Tue 4/7
10:30 am-12:15 pm
Nonstop2h 45m
Denver Intl
Fri 4/10
5:20 am-12:50 pm
1 stop6h 30m
$217
Showing 1-10 of 44 resultsSorted by cheapest first
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.
ORD-DEN
MDW-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
ORD-DEN
MDW-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 February 27, 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 $58). Flying from Chicago to Breckenridge in July is currently the most expensive (average of $114). 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 March 6, 2026.
It’s typically best to fly out from Chicago to Breckenridge at noon. Doing so could potentially save you 25% 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 February 21, 2026.
Travelers seeking maximum savings on their Chicago to Breckenridge flight should consider departing on Saturday evenings 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.
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 March 6, 2026.
See what other customers who have flown with Southwest, United Airlines, and JetBlue 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.
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
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.
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
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Top destinations
Alternative routes for Chicago to Breckenridge
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Breckenridge by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Breckenridge by cabin class
Find flights from Chicago to Breckenridge, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Breckenridge flights
Browse other Chicago and Breckenridge flight options. Last updated on March 6, 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 March 6, 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 March 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$151 | Average$340 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$155 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$296 | FlexibilityNo cancel fee | On-time63% |