$88+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Apr 23 — Apr 301
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 March 24, 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 24, 2026.
This Expedia deal was found by Cheapflights users on 3/20. 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.
Mon 4/135:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Fri 4/2410:38 am
DEN
- MDW
1 stop10h 12m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 3/20. 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.
Wed 5/61:59 pm
ORD
- DEN
1 stop9h 25m
Frontier
Mon 5/1111:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 6/59:42 pm
ORD
- DEN
Nonstop3h 10m
Frontier
Mon 6/84:59 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/20![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 4/96:00 pm
ORD
- DEN
1 stop6h 58m
Frontier
Sat 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/22![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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
Wed 4/158:25 pm
DEN
- ORD
1 stop14h 48m
Frontier
Deal found 3/23![Frontier logo]()
$163
This Trip.com deal was found by Cheapflights users on 3/22. 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 5/73:07 pm
MDW
- DEN
1 stop6h 36m
Frontier
Tue 5/127:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 3/22![Frontier logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 3/22. 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 5/214:05 pm
ORD
- DEN
1 stop8h 53m
Frontier
Tue 5/2611:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 3/22![Frontier logo]()
$164
This Southwest deal was found by Cheapflights users on 3/22. 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 4/215:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Tue 4/2811:05 am
DEN
- MDW
1 stop4h 30m
Southwest
Deal found 3/22![Southwest logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 5/279:42 pm
ORD
- DEN
Nonstop3h 10m
Frontier
Mon 6/84:59 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/20![Frontier logo]()
$165
This Super.com deal was found by Cheapflights users on 3/21. 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 4/286:10 am
MDW
- DEN
1 stop7h 04m
Frontier
Tue 4/2811:59 pm
DEN
- MDW
1 stop30h 22m
Frontier
Deal found 3/21![Frontier logo]()
$166
This Super.com deal was found by Cheapflights users on 3/23. 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 4/1610:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Mon 4/206:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/23![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 3/20. 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 5/289:42 pm
ORD
- DEN
Nonstop3h 10m
Frontier
Mon 6/84:59 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/20![Frontier logo]()
$167
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 24, 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 24, 2026.
This Southwest deal was found by Cheapflights users on 3/22. 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
Sat 5/166:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/22![Southwest logo]()
$176
This United Airlines deal was found by Cheapflights users on 3/23. 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 5/1411:00 pm
ORD
- DEN
Nonstop2h 56m
United Airlines
Sun 5/179:20 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Deal found 3/23![United Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 3/21. 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 7/412:46 pm
ORD
- DEN
1 stop7h 45m
Delta
Thu 7/911:08 am
DEN
- ORD
1 stop4h 51m
Delta
Deal found 3/21![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 3/23. 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 5/1311:55 am
ORD
- DEN
2 stops8h 30m
Southwest
Wed 5/206:15 am
DEN
- ORD
1 stop6h 00m
Southwest
Deal found 3/23![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 3/22. 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 5/19:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Wed 5/611:05 am
DEN
- MDW
1 stop4h 30m
Southwest
Deal found 3/22![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 3/21. 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 6/1910:55 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Mon 6/227:40 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 3/21![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 3/22. 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 5/143:45 pm
ORD
- DEN
2 stops9h 00m
Southwest
Mon 5/186:05 am
DEN
- ORD
1 stop6h 10m
Southwest
Deal found 3/22![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 3/19. 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 7/217:10 am
ORD
- DEN
1 stop8h 57m
Delta
Tue 7/286:05 am
DEN
- ORD
1 stop7h 15m
Delta
Deal found 3/19![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 3/19. 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 4/113:05 pm
ORD
- DEN
Nonstop3h 00m
Southwest
Sat 4/1810:50 am
DEN
- ORD
Nonstop2h 30m
Southwest
Deal found 3/19![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 3/19. 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 7/35:25 pm
MDW
- DEN
1 stop7h 20m
Delta
Thu 7/912:55 am
DEN
- MDW
1 stop6h 47m
Delta
Deal found 3/19![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 3/20. 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 7/49:20 am
MDW
- DEN
1 stop4h 33m
Delta
Fri 7/1012:55 am
DEN
- MDW
1 stop6h 47m
Delta
Deal found 3/20![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 3/19. 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 5/49:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Mon 5/116:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/19![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 3/20. 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 7/42:00 pm
MDW
- DEN
1 stop6h 58m
Delta
Tue 7/712:55 am
DEN
- MDW
1 stop6h 47m
Delta
Deal found 3/20![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 3/19. 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 4/2811:55 am
ORD
- DEN
2 stops11h 40m
Southwest
Tue 5/51:15 pm
DEN
- ORD
1 stop8h 40m
Southwest
Deal found 3/19![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 3/20. 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 5/276:50 pm
MDW
- DEN
1 stop6h 15m
Southwest
Sun 5/315:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 3/20![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 3/21. 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
Mon 5/46:05 am
DEN
- ORD
1 stop6h 10m
Southwest
Deal found 3/21![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 3/19. 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 5/15:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Sun 5/35:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 3/19![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 3/20. 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 6/138:30 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Sun 6/285:50 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 3/20![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 3/20. 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 4/93:45 pm
ORD
- DEN
2 stops9h 00m
Southwest
Thu 4/167:00 am
DEN
- ORD
1 stop7h 30m
Southwest
Deal found 3/20![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 3/21. 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 5/114:05 pm
MDW
- DEN
1 stop4h 15m
Southwest
Mon 5/118:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/21![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 3/19. 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 6/54:05 pm
MDW
- DEN
1 stop5h 00m
Southwest
Sun 6/78:55 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/19![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 3/19. 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 5/162:05 pm
ORD
- DEN
2 stops9h 15m
Southwest
Sun 5/1711:50 pm
DEN
- ORD
1 stop8h 55m
Southwest
Deal found 3/19![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 3/22. 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 5/83:45 pm
ORD
- DEN
2 stops9h 00m
Southwest
Sun 5/106:25 am
DEN
- ORD
1 stop5h 50m
Southwest
Deal found 3/22![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 3/22. 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 5/211:30 pm
MDW
- DEN
1 stop4h 15m
Southwest
Tue 5/265:55 am
DEN
- MDW
1 stop4h 40m
Southwest
Deal found 3/22![Southwest logo]()
$262
Last-minute flights from Chicago to BreckenridgeDiscover last-minute flight deals from Chicago to Breckenridge. Data last updated March 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Breckenridge. Data last updated March 24, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 4/83:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Mon 4/135:49 pm
DEN
- ORD
1 stop20h 28m
Frontier
Deal found 3/23![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 4/96:00 pm
ORD
- DEN
1 stop6h 58m
Frontier
Sat 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/22![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 3/20. 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
Fri 4/176:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/20![Frontier logo]()
$164
This Expedia deal was found by Cheapflights users on 3/20. 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.
Mon 4/135:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Fri 4/2410:38 am
DEN
- MDW
1 stop10h 12m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Super.com deal was found by Cheapflights users on 3/21. 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.
Mon 4/132:29 pm
ORD
- DEN
Nonstop3h 11m
Frontier
Mon 4/206:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/21![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 4/1710:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Mon 4/206:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/23![Frontier logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 4/1710:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Fri 4/2411:59 pm
DEN
- ORD
1 stop10h 34m
Frontier
Deal found 3/23![Frontier logo]()
$172
This Southwest deal was found by Cheapflights users on 3/22. 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 4/216:30 am
MDW
- DEN
Nonstop2h 40m
Southwest
Tue 4/2811:45 am
DEN
- MDW
1 stop3h 55m
Southwest
Deal found 3/22![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 3/22. 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 4/213:45 pm
ORD
- DEN
1 stop6h 10m
Southwest
Tue 4/2811:25 am
DEN
- ORD
Nonstop2h 35m
Southwest
Deal found 3/22![Southwest logo]()
$169
This Super.com deal was found by Cheapflights users on 3/21. 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 4/286:10 am
MDW
- DEN
1 stop7h 04m
Frontier
Tue 4/2811:59 pm
DEN
- MDW
1 stop30h 22m
Frontier
Deal found 3/21![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/292:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Tue 5/57:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 3/18![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/308:25 am
MDW
- DEN
1 stop15h 24m
Frontier
Tue 5/57:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 3/19![Frontier logo]()
$171
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 24, 2026.
Search for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated March 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 5/1912:40 pm
ORD
- DEN
1 stop18h 53m
Frontier
Deal found 3/19![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/193:07 pm
MDW
- DEN
1 stop16h 26m
Frontier
Deal found 3/23![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 3/20. 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 4/96:00 pm
ORD
- DEN
1 stop6h 58m
Frontier
Deal found 3/20![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 3/18. 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 4/105:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 3/18![Frontier logo]()
$89
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:10 am
MDW
- DEN
1 stop7h 04m
Frontier
Deal found 3/23![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 6/209:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 3/19![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 3/20. 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 4/96:00 am
MDW
- DEN
1 stop7h 09m
Frontier
Deal found 3/20![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 3/21. 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 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Deal found 3/21![Frontier logo]()
$93
This Trip.com deal was found by Cheapflights users on 3/23. 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.
Tue 4/72:56 pm
MDW
- DEN
1 stop9h 08m
Frontier
Deal found 3/23![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 3/23. 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 5/37:21 pm
ORD
- DEN
1 stop15h 24m
Frontier
Deal found 3/23![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 3/20. 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 4/55:05 am
MDW
- DEN
1 stop28h 16m
Frontier
Deal found 3/20![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 3/23. 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 4/2911:55 am
ORD
- DEN
2 stops11h 40m
Southwest
Deal found 3/23![Southwest logo]()
$95
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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $160 (Frontier) |
One-way from | $88 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $274 |
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 24, 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
Quickest round-trip
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 5/13
6:30 am-8:10 am
Nonstop2h 40m
Denver Intl
Sat 5/16
6:30 am-9:50 am
Nonstop2h 20m
$176
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Wed 5/13
11:55 am-7:25 pm
2 stops8h 30m
Denver Intl
Wed 5/20
6:15 am-1:15 pm
1 stop6h 00m
$184
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 5/1
9:35 pm-11:15 pm
Nonstop2h 40m
Denver Intl
Wed 5/6
11:05 am-4:35 pm
1 stop4h 30m
$197
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Thu 5/14
3:45 pm-11:45 pm
2 stops9h 00m
Denver Intl
Mon 5/18
6:05 am-1:15 pm
1 stop6h 10m
$217
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Thu 5/14
11:00 pm-12:56 am
Nonstop2h 56m
Denver Intl
Sun 5/17
9:20 pm-12:58 am
Nonstop2h 38m
$218
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Sat 4/11
3:05 pm-5:05 pm
Nonstop3h 00m
Denver Intl
Sat 4/18
10:50 am-2:20 pm
Nonstop2h 30m
$219
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Mon 5/4
9:35 pm-11:15 pm
Nonstop2h 40m
Denver Intl
Mon 5/11
6:35 am-9:55 am
Nonstop2h 20m
$221
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Tue 4/28
11:55 am-10:35 pm
2 stops11h 40m
Denver Intl
Tue 5/5
1:15 pm-10:55 pm
1 stop8h 40m
$226
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 5/27
6:50 pm-12:05 am
1 stop6h 15m
Denver Intl
Sun 5/31
5:55 am-9:20 am
Nonstop2h 25m
$233
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Sat 5/2
3:05 pm-5:05 pm
Nonstop3h 00m
Denver Intl
Mon 5/4
6:05 am-1:15 pm
1 stop6h 10m
$241
Showing 1-10 of 45 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.
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 March 13, 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, April is the cheapest month in which you can book a flight from Chicago to Breckenridge (average of $76). Flying from Chicago to Breckenridge in February is currently the most expensive (average of $113). 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 24, 2026.
It’s typically best to fly out from Chicago to Breckenridge at noon. Doing so could potentially save you 24% 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 March 14, 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 March 24, 2026.
The most flights from CHI to BK9 are scheduled on a Monday (62 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (34 on average).
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 24, 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.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
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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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 24, 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 24, 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$168 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$151 | Average$340 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$301 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$391 | FlexibilityNo cancel fee | On-time69% |