$89+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
May 17 — May 241
Round-trip
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 85 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 April 17, 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 April 17, 2026.
This Super.com deal was found by Cheapflights users on 4/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Mon 7/135:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/12![Frontier logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 6/89:54 pm
DEN
- ORD
1 stop12h 39m
Frontier
Deal found 4/14![Frontier logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Wed 5/2711:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/14![Frontier logo]()
$158
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:09 pm
ORD
- DEN
1 stop10h 50m
Frontier
Wed 5/66:30 am
DEN
- ORD
1 stop12h 21m
Frontier
Deal found 4/14![Frontier logo]()
$159
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:24 pm
MDW
- DEN
1 stop11h 00m
Frontier
Fri 5/1511:54 pm
DEN
- MDW
1 stop10h 10m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:28 pm
ORD
- DEN
1 stop7h 01m
Frontier
Sat 5/911:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Mon 5/1111:54 pm
DEN
- MDW
1 stop10h 15m
Frontier
Deal found 4/14![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Tue 7/217:00 am
DEN
- ORD
1 stop16h 42m
Frontier
Deal found 4/14![Frontier logo]()
$161
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Wed 7/811:42 pm
DEN
- ORD
1 stop7h 21m
Frontier
Deal found 4/14![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:50 am
ORD
- DEN
Nonstop3h 03m
Frontier
Fri 5/85:27 pm
DEN
- ORD
1 stop28h 34m
Frontier
Deal found 4/14![Frontier logo]()
$163
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:50 am
ORD
- DEN
1 stop7h 24m
Frontier
Mon 5/114:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/14![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- DEN
2 stops14h 29m
Frontier
Tue 5/197:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 4/12![Frontier logo]()
$165
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 April 17, 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 April 17, 2026.
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:30 am
ORD
- DEN
1 stop4h 35m
Delta
Thu 6/1812:59 am
DEN
- ORD
1 stop6h 06m
Delta
Deal found 4/15![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 4/13. 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 6/105:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Wed 6/176:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 4/13![Southwest logo]()
$201
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Tue 5/269:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 4/14![United Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:46 pm
ORD
- DEN
1 stop8h 08m
Delta
Wed 6/176:00 am
DEN
- ORD
1 stop4h 31m
Delta
Deal found 4/15![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:41 pm
MDW
- DEN
1 stop7h 53m
Delta
Wed 7/86:05 am
DEN
- MDW
1 stop5h 28m
Delta
Deal found 4/16![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:06 pm
MDW
- DEN
1 stop5h 21m
Delta
Sat 7/1112:11 pm
DEN
- MDW
1 stop4h 41m
Delta
Deal found 4/15![Delta logo]()
$167
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:39 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Tue 6/99:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 4/14![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:20 am
MDW
- DEN
Nonstop2h 35m
Southwest
Tue 6/96:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 4/14![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:05 pm
ORD
- DEN
Nonstop3h 00m
Southwest
Mon 5/1111:25 am
DEN
- ORD
Nonstop2h 35m
Southwest
Deal found 4/14![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 4/13. 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 5/95:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/118:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/13![Southwest logo]()
$221
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:00 am
ORD
- DEN
Nonstop2h 42m
United Airlines
Tue 10/138:34 pm
DEN
- ORD
Nonstop2h 23m
United Airlines
Deal found 4/15![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:50 pm
ORD
- DEN
1 stop7h 39m
Delta
Sun 8/306:45 am
DEN
- ORD
1 stop4h 54m
Delta
Deal found 4/15![Delta logo]()
$206
This United Airlines deal was found by Cheapflights users on 4/12. 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.
Fri 10/29:45 pm
ORD
- DEN
Nonstop2h 33m
United Airlines
Mon 10/57:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 4/12![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Wed 5/275:55 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Deal found 4/16![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 4/13. 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 8/1211:30 am
ORD
- DEN
1 stop7h 01m
Delta
Tue 8/186:45 am
DEN
- ORD
1 stop4h 54m
Delta
Deal found 4/13![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 4/12. 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.
Sat 9/195:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Sat 9/266:15 am
DEN
- ORD
Nonstop2h 28m
United Airlines
Deal found 4/12![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 4/12. 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.
Thu 5/149:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/186:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/12![Southwest logo]()
$243
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Sun 8/166:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Deal found 4/17![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 4/12. 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.
Thu 5/216:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/258:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/12![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 4/13. 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.
Fri 7/33:55 pm
ORD
- DEN
1 stop5h 07m
Delta
Mon 7/66:00 am
DEN
- ORD
1 stop4h 31m
Delta
Deal found 4/13![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 4/12. 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.
Fri 5/226:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/258:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/12![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Fri 7/178:50 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/15![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 4/13. 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 7/65:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Fri 7/106:25 pm
DEN
- MDW
1 stop4h 50m
Southwest
Deal found 4/13![Southwest logo]()
$265
Last-minute flights from Chicago to BreckenridgeDiscover last-minute flight deals from Chicago to Breckenridge. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Breckenridge. Data last updated April 17, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:09 pm
ORD
- DEN
1 stop10h 50m
Frontier
Wed 5/66:30 am
DEN
- ORD
1 stop12h 21m
Frontier
Deal found 4/14![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:28 pm
ORD
- DEN
1 stop7h 01m
Frontier
Sat 5/911:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:50 am
ORD
- DEN
1 stop7h 24m
Frontier
Mon 5/114:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/14![Frontier logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:50 am
ORD
- DEN
Nonstop3h 03m
Frontier
Fri 5/85:27 pm
DEN
- ORD
1 stop28h 34m
Frontier
Deal found 4/14![Frontier logo]()
$163
This Super.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Sun 5/104:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/15![Frontier logo]()
$157
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Mon 5/1111:54 pm
DEN
- MDW
1 stop10h 15m
Frontier
Deal found 4/14![Frontier logo]()
$161
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:24 pm
MDW
- DEN
1 stop11h 00m
Frontier
Fri 5/1511:54 pm
DEN
- MDW
1 stop10h 10m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
- DEN
2 stops14h 29m
Frontier
Tue 5/197:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 4/12![Frontier logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 5/259:54 pm
DEN
- ORD
1 stop12h 46m
Frontier
Deal found 4/14![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/12. 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.
Fri 5/229:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 6/14:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/12![Frontier logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Wed 5/2711:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/14![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:37 pm
ORD
- DEN
Nonstop3h 07m
Multiple Airlines
Mon 6/16:20 am
DEN
- ORD
1 stop11h 46m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$162
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 April 17, 2026.
Search for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:28 pm
ORD
- DEN
1 stop7h 01m
Frontier
Deal found 4/14![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- DEN
1 stop7h 14m
Frontier
Deal found 4/14![Frontier logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/284:05 pm
ORD
- DEN
1 stop8h 53m
Frontier
Deal found 4/14![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 4/14![Frontier logo]()
$90
This Trip.com deal was found by Cheapflights users on 4/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Deal found 4/12![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 4/13. 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 4/1910:50 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 4/13![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- DEN
1 stop6h 59m
Frontier
Deal found 4/14![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:50 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 4/14![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/214:05 pm
ORD
- DEN
1 stop8h 53m
Frontier
Deal found 4/14![Frontier logo]()
$94
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:22 am
MDW
- DEN
1 stop5h 37m
Delta
Deal found 4/14![Delta logo]()
$94
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:04 pm
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 4/14![Frontier logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:04 pm
ORD
- DEN
1 stop14h 00m
Frontier
Deal found 4/14![Frontier logo]()
$96
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 April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $156 (Super.com) |
One-way from | $89 (Super.com) |
Popular in | March |
Cheapest in | October |
Average price | $259 |
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 April 17, 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 6/9
6:30 am-10:05 am
1 stop4h 35m
Denver Intl
Thu 6/18
12:59 am-8:05 am
1 stop6h 06m
$167
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Thu 6/11
1:46 pm-8:54 pm
1 stop8h 08m
Denver Intl
Wed 6/17
6:00 am-11:31 am
1 stop4h 31m
$167
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 6/30
5:41 pm-12:34 am
1 stop7h 53m
Denver Intl
Wed 7/8
6:05 am-12:33 pm
1 stop5h 28m
$167
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 7/7
7:06 pm-11:27 pm
1 stop5h 21m
Denver Intl
Sat 7/11
12:11 pm-5:52 pm
1 stop4h 41m
$167
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 6/10
5:30 am-7:05 am
Nonstop2h 35m
Denver Intl
Wed 6/17
6:15 am-9:40 am
Nonstop2h 25m
$201
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Thu 8/27
3:50 pm-10:29 pm
1 stop7h 39m
Denver Intl
Sun 8/30
6:45 am-12:39 pm
1 stop4h 54m
$206
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Sat 5/23
6:00 am-7:41 am
Nonstop2h 41m
Denver Intl
Tue 5/26
9:05 pm-12:44 am
Nonstop2h 39m
$211
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Sat 6/6
9:39 pm-11:37 pm
Nonstop2h 58m
Denver Intl
Tue 6/9
9:05 pm-12:44 am
Nonstop2h 39m
$211
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Sat 6/6
7:20 am-8:55 am
Nonstop2h 35m
Denver Intl
Tue 6/9
6:15 am-9:40 am
Nonstop2h 25m
$211
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Sat 5/9
3:05 pm-5:05 pm
Nonstop3h 00m
Denver Intl
Mon 5/11
11:25 am-3:00 pm
Nonstop2h 35m
$221
Showing 1-10 of 43 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 April 10, 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 85 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 April 17, 2026.
It’s typically best to fly out from Chicago to Breckenridge at noon. Doing so could potentially save you 17% 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 April 11, 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.
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 April 17, 2026.
The most flights from CHI to BK9 are scheduled on a Thursday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 April 17, 2026.
See what other customers who have flown with Southwest,United Airlines, andJetBlue 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.
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
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 April 17, 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 April 17, 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 April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$239 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$152 | Average$335 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$154 | Average$304 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$393 | FlexibilityNo cancel fee | On-time69% |