$103+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
Aug 22 — Aug 291
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 Wednesday or Friday and return on a Friday
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 July 23, 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 July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Wed 8/125:30 pm
ORD
- DEN
1 stop15h 44m
Frontier
Wed 8/267:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/22![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sat 8/159:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Wed 8/197:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/22![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Wed 8/125:30 pm
ORD
- DEN
1 stop15h 44m
Frontier
Sat 8/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 7/23![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/182:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Wed 8/197:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/23![Frontier logo]()
$163
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/611:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Sat 10/106:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Deal found 7/22![Frontier logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Mon 8/175:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 7/19![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sat 9/192:46 pm
ORD
- DEN
1 stop10h 07m
Frontier
Wed 9/238:40 am
DEN
- ORD
1 stop11h 54m
Frontier
Deal found 7/22![Frontier logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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.
Fri 9/42:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Sun 9/69:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/22![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Thu 10/2911:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Mon 11/28:40 am
DEN
- ORD
1 stop11h 54m
Frontier
Deal found 7/20![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Sat 9/59:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/21![Frontier logo]()
$169
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Thu 8/279:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/19![Frontier logo]()
$170
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Thu 9/105:56 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Deal found 7/21![Frontier logo]()
$171
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 July 23, 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 July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 8/299:25 am
MDW
- DEN
Nonstop2h 35m
Southwest
Mon 8/316:30 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Deal found 7/21![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:05 am
ORD
- DEN
1 stop7h 58m
Delta
Sat 11/146:45 am
DEN
- ORD
1 stop4h 52m
Delta
Deal found 7/22![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Sat 10/178:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Deal found 7/18![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 7/22. 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 9/36:45 am
MDW
- DEN
Nonstop2h 30m
Southwest
Tue 9/811:15 am
DEN
- MDW
1 stop3h 45m
Southwest
Deal found 7/22![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:13 pm
MDW
- DEN
1 stop5h 22m
Delta
Sat 9/128:45 am
DEN
- MDW
1 stop6h 15m
Delta
Deal found 7/22![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 7/20. 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.
Fri 9/114:25 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Mon 9/148:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/20![Southwest logo]()
$216
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:55 am
ORD
- DEN
Nonstop2h 50m
United Airlines
Sun 8/305:48 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Deal found 7/18![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 7/22. 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 9/11:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Thu 10/111:20 am
DEN
- MDW
1 stop4h 55m
Southwest
Deal found 7/22![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 7/21. 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.
Tue 8/116:45 pm
ORD
- DEN
1 stop5h 49m
Delta
Wed 8/1212:59 am
DEN
- ORD
1 stop5h 57m
Delta
Deal found 7/21![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 7/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:40 am
MDW
- DEN
Nonstop2h 30m
Southwest
Tue 8/186:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/18![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Sun 10/116:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Deal found 7/18![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:30 am
ORD
- DEN
1 stop7h 26m
Delta
Fri 12/46:45 am
DEN
- ORD
1 stop4h 52m
Delta
Deal found 7/23![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 7/19. 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 8/186:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Tue 8/257:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 7/19![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 7/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:55 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Sun 8/168:31 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Deal found 7/19![United Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:00 pm
ORD
- DEN
1 stop8h 15m
Delta
Sun 10/1812:59 am
DEN
- ORD
1 stop6h 04m
Delta
Deal found 7/22![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 7/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Sat 9/266:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/18![Southwest logo]()
$233
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 8/125:55 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Wed 8/126:18 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Deal found 7/21![United Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:25 am
ORD
- DEN
1 stop4h 43m
Delta
Sun 9/276:30 am
DEN
- ORD
1 stop5h 29m
Delta
Deal found 7/22![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 7/19. 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 11/139:30 am
ORD
- DEN
1 stop7h 26m
Delta
Wed 11/186:45 am
DEN
- ORD
1 stop4h 52m
Delta
Deal found 7/19![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 7/21. 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.
Thu 8/275:50 pm
MDW
- DEN
1 stop5h 10m
Southwest
Sun 8/306:10 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 7/21![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 7/19. 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 8/248:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Fri 8/288:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/19![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 7/20. 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 11/213:50 pm
ORD
- DEN
1 stop5h 10m
Delta
Mon 11/234:00 pm
DEN
- ORD
1 stop4h 34m
Delta
Deal found 7/20![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 7/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:50 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Tue 10/610:45 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/18![Southwest logo]()
$246
Last-minute flights from Chicago to BreckenridgeDiscover last-minute flight deals from Chicago to Breckenridge. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Breckenridge. Data last updated July 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Thu 9/105:56 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Deal found 7/21![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Wed 8/125:30 pm
ORD
- DEN
1 stop15h 44m
Frontier
Wed 8/267:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/22![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Wed 8/125:30 pm
ORD
- DEN
1 stop15h 44m
Frontier
Sat 8/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 7/23![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Mon 8/175:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 7/19![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sat 8/159:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Wed 8/197:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/22![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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.
Mon 8/179:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Thu 8/209:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/22![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/182:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Wed 8/197:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/23![Frontier logo]()
$163
This Super.com deal was found by Cheapflights users on 7/18. 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.
Tue 8/182:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Sun 8/239:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/18![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Thu 8/279:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/19![Frontier logo]()
$170
This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 8/207:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Thu 8/276:30 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Deal found 7/23![Southwest logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Mon 8/245:46 pm
ORD
- DEN
1 stop15h 28m
Frontier
Wed 9/29:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/19![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Fri 8/282:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Mon 8/3110:43 am
DEN
- ORD
1 stop8h 16m
Frontier
Deal found 7/18![Frontier logo]()
$164
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 July 23, 2026.
Search for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/22. 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 8/208:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/22![Southwest logo]()
$103
This United Airlines deal was found by Cheapflights users on 7/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 7/22![United Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sat 9/57:11 am
ORD
- DEN
1 stop27h 08m
Frontier
Deal found 7/18![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/205:42 pm
ORD
- DEN
1 stop6h 32m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$106
This Southwest deal was found by Cheapflights users on 7/22. 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 8/129:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/22![Southwest logo]()
$108
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:15 pm
ORD
- DEN
Nonstop2h 44m
American Airlines
Deal found 7/22![American Airlines logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/19![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/198:45 am
ORD
- DEN
1 stop24h 29m
Frontier
Deal found 7/18![Frontier logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 7/20. 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 8/79:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/20![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Mon 8/107:05 am
ORD
- DEN
1 stop26h 58m
Frontier
Deal found 7/18![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 7/22. 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.
Sat 8/151:45 pm
MDW
- DEN
1 stop5h 55m
Southwest
Deal found 7/22![Southwest logo]()
$113
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/19![Frontier logo]()
$113
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 July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $160 (Kiwi.com) |
One-way from | $103 (Southwest) |
Popular in | March |
Cheapest in | October |
Average price | $298 |
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 July 23, 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
MDW - DEN
MDWDEN
Chicago Midway
Sat 8/29
9:25 am-11:00 am
Nonstop2h 35m
Denver Intl
Mon 8/31
6:30 pm-10:00 pm
Nonstop2h 30m
$205
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Thu 9/3
6:45 am-8:15 am
Nonstop2h 30m
Denver Intl
Tue 9/8
11:15 am-4:00 pm
1 stop3h 45m
$211
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 9/11
4:25 pm-6:00 pm
Nonstop2h 35m
Denver Intl
Mon 9/14
8:25 pm-11:45 pm
Nonstop2h 20m
$216
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 9/1
1:55 pm-7:50 pm
2 stops6h 55m
Denver Intl
Thu 10/1
11:20 am-5:15 pm
1 stop4h 55m
$221
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Tue 11/10
7:05 am-2:03 pm
1 stop7h 58m
Denver Intl
Sat 11/14
6:45 am-12:37 pm
1 stop4h 52m
$225
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Mon 10/12
6:00 am-7:39 am
Nonstop2h 39m
Denver Intl
Sat 10/17
8:29 pm-11:59 pm
Nonstop2h 30m
$227
Quickest round-trip
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 8/11
6:40 am-8:10 am
Nonstop2h 30m
Denver Intl
Tue 8/18
6:30 am-9:50 am
Nonstop2h 20m
$227
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 8/18
6:00 pm-7:40 pm
Nonstop2h 40m
Denver Intl
Tue 8/25
7:25 pm-10:50 pm
Nonstop2h 25m
$227
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 9/23
9:00 am-12:55 pm
1 stop4h 55m
Denver Intl
Sat 9/26
6:00 am-9:20 am
Nonstop2h 20m
$233
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 9/9
7:13 pm-11:35 pm
1 stop5h 22m
Denver Intl
Sat 9/12
8:45 am-4:00 pm
1 stop6h 15m
$235
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.
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
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 July 23, 2026.
It’s typically best to fly out from Chicago to Breckenridge at noon. Doing so could potentially save you 12% on the flight price compared to flying in the evening, which is usually more expensive.
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 July 23, 2026.
The most flights from CHI to BK9 are scheduled on a Monday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago to Breckenridge?
Airfare is below average for this route at the moment.
Chicago to Breckenridge flights typically cost between $198 and $330 in August.The cheapest round-trip price found within the last 5 days was $160 on Frontier (Aug 12-Aug 26).
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 July 18, 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 July 23, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Breckenridge have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
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 July 23, 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 July 23, 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 6 airlines flying from Chicago to Breckenridge
Discover the top 6 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$175 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$105 | Average$284 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$145 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$151 | Average$348 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$346 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$168 | Average$401 | FlexibilityNo cancel fee | On-time69% |