$90+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DEN
May 24 — May 311
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 September or October, 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 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 April 24, 2026.
This Priceline deal was found by Cheapflights users on 4/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- DEN
1 stop11h 20m
Frontier
Wed 5/1311:54 pm
DEN
- MDW
1 stop10h 15m
Frontier
Deal found 4/20![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Mon 5/119:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Thu 5/1411:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/20![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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.
Tue 7/149:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Fri 7/177:00 am
DEN
- ORD
1 stop16h 42m
Frontier
Deal found 4/20![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/74:05 pm
ORD
- DEN
1 stop25h 26m
Frontier
Mon 5/114:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/19![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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.
Tue 5/59:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Wed 5/610:00 am
DEN
- ORD
1 stop12h 01m
Frontier
Deal found 4/20![Frontier logo]()
$163
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:11 pm
ORD
- DEN
1 stop16h 13m
Frontier
Tue 5/2611:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/21![Frontier logo]()
$164
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:52 pm
MDW
- DEN
1 stop31h 19m
Frontier
Sat 5/2310:00 am
DEN
- MDW
1 stop11h 02m
Frontier
Deal found 4/23![Frontier logo]()
$165
This Super.com deal was found by Cheapflights users on 4/21. 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 5/139:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Fri 5/154:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/21![Frontier logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares 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
Sat 7/1111:49 pm
DEN
- ORD
1 stop22h 25m
Frontier
Deal found 4/21![Frontier logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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 5/229:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 6/15:27 pm
DEN
- ORD
1 stop28h 34m
Frontier
Deal found 4/19![Frontier logo]()
$167
This Trip.com deal was found by Cheapflights users on 4/20. 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.
Tue 5/56:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Tue 5/127:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 4/20![Frontier logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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 6/59:04 pm
ORD
- DEN
1 stop14h 00m
Frontier
Tue 6/95:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/20![Frontier logo]()
$168
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 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 April 24, 2026.
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mon 9/288:45 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Wed 9/301:55 pm
DEN
- MDW
1 stop4h 30m
Southwest
Deal found 4/23![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 6/61:59 pm
MDW
- DEN
1 stop7h 16m
Delta
Tue 6/96:05 am
DEN
- MDW
1 stop5h 31m
Delta
Deal found 4/23![Delta logo]()
$211
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 7/47:05 am
ORD
- DEN
Nonstop2h 50m
United Airlines
Tue 7/77:40 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Deal found 4/22![United Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 4/21. 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.
Wed 9/211:10 am
MDW
- DEN
1 stop4h 50m
Southwest
Sat 9/511:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Deal found 4/21![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 6/56:36 pm
MDW
- DEN
1 stop5h 22m
Delta
Wed 6/102:15 pm
DEN
- MDW
1 stop7h 02m
Delta
Deal found 4/23![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 4/20. 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.
Tue 6/95:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Sat 6/135:15 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/20![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 4/23. 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.
Fri 6/59:25 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Tue 6/910:25 am
DEN
- MDW
2 stops5h 35m
Southwest
Deal found 4/23![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 6/56:36 pm
MDW
- DEN
1 stop5h 22m
Delta
Mon 6/812:12 pm
DEN
- MDW
1 stop5h 06m
Delta
Deal found 4/23![Delta logo]()
$243
This Southwest deal was found by Cheapflights users on 4/19. 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 5/198:50 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Wed 5/276:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/19![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 6/55:19 pm
ORD
- DEN
1 stop6h 39m
Delta
Sun 6/76:05 am
DEN
- ORD
1 stop5h 59m
Delta
Deal found 4/23![Delta logo]()
$273
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/18:20 pm
ORD
- DEN
Nonstop2h 59m
United Airlines
Mon 5/48:20 pm
DEN
- ORD
Nonstop2h 37m
United Airlines
Deal found 4/21![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 4/19. 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 5/294:15 pm
ORD
- DEN
1 stop8h 30m
Southwest
Mon 6/15:20 am
DEN
- ORD
1 stop6h 30m
Southwest
Deal found 4/19![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 5/225:19 pm
ORD
- DEN
1 stop6h 39m
Delta
Sun 5/3112:55 am
DEN
- ORD
1 stop6h 50m
Delta
Deal found 4/23![Delta logo]()
$278
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:40 pm
ORD
- DEN
Nonstop2h 56m
United Airlines
Sat 5/169:20 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Deal found 4/20![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 4/20. 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 6/45:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Thu 6/115:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 4/20![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 4/21. 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.
Fri 6/1911:30 am
ORD
- DEN
1 stop7h 09m
Delta
Thu 6/2512:59 am
DEN
- ORD
1 stop6h 06m
Delta
Deal found 4/21![Delta logo]()
$285
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Sat 5/237:05 am
ORD
- DEN
Nonstop2h 50m
United Airlines
Sat 5/237:10 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 4/19![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 4/20. 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 5/136:30 am
MDW
- DEN
Nonstop2h 40m
Southwest
Wed 5/1310:55 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/20![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 4/19. 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.
Sun 5/246:24 am
ORD
- DEN
1 stop4h 56m
Delta
Sun 5/244:41 pm
DEN
- ORD
1 stop6h 27m
Delta
Deal found 4/19![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 4/23. 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 7/89:05 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Sat 7/118:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 4/23![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 4/20. 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 5/611:55 am
ORD
- DEN
2 stops10h 00m
Southwest
Wed 5/136:15 am
DEN
- ORD
1 stop5h 35m
Southwest
Deal found 4/20![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mon 4/276:15 pm
ORD
- DEN
Nonstop2h 50m
Southwest
Fri 5/17:00 am
DEN
- ORD
1 stop7h 30m
Southwest
Deal found 4/23![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 4/19. 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 5/14:15 pm
ORD
- DEN
2 stops8h 10m
Southwest
Wed 5/64:25 pm
DEN
- ORD
1 stop6h 30m
Southwest
Deal found 4/19![Southwest logo]()
$386
Last-minute flights from Chicago to BreckenridgeDiscover last-minute flight deals from Chicago to Breckenridge. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Breckenridge. Data last updated April 24, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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.
Tue 5/59:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Wed 5/610:00 am
DEN
- ORD
1 stop12h 01m
Frontier
Deal found 4/20![Frontier logo]()
$163
This Trip.com deal was found by Cheapflights users on 4/20. 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.
Tue 5/56:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Tue 5/127:00 am
DEN
- MDW
1 stop6h 12m
Frontier
Deal found 4/20![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/74:05 pm
ORD
- DEN
1 stop25h 26m
Frontier
Mon 5/114:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/19![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Mon 5/119:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Thu 5/1411:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/20![Frontier logo]()
$160
This Priceline deal was found by Cheapflights users on 4/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- DEN
1 stop11h 20m
Frontier
Wed 5/1311:54 pm
DEN
- MDW
1 stop10h 15m
Frontier
Deal found 4/20![Frontier logo]()
$160
This Super.com deal was found by Cheapflights users on 4/21. 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 5/139:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Fri 5/154:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/21![Frontier logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
Wed 5/139:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Sun 5/174:54 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 4/22![Frontier logo]()
$166
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:52 pm
MDW
- DEN
1 stop31h 19m
Frontier
Sat 5/2310:00 am
DEN
- MDW
1 stop11h 02m
Frontier
Deal found 4/23![Frontier logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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 5/229:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 6/15:27 pm
DEN
- ORD
1 stop28h 34m
Frontier
Deal found 4/19![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Sat 5/239:37 pm
ORD
- DEN
Nonstop3h 07m
Multiple Airlines
Wed 5/275:05 am
DEN
- ORD
1 stop8h 58m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:11 pm
ORD
- DEN
1 stop16h 13m
Frontier
Tue 5/2611:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 4/21![Frontier logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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.
Tue 5/269:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Mon 6/15:27 pm
DEN
- ORD
1 stop28h 34m
Frontier
Deal found 4/20![Frontier logo]()
$168
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 24, 2026.
Search for one-way flight options from Chicago to Breckenridge. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- DEN
1 stop9h 04m
Frontier
Deal found 4/21![Frontier logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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.
Tue 5/191:59 pm
ORD
- DEN
1 stop9h 25m
Frontier
Deal found 4/20![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/131:59 pm
ORD
- DEN
1 stop9h 25m
Frontier
Deal found 4/23![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 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 4/21![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 4/20. 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.
Fri 5/89:37 pm
ORD
- DEN
Nonstop3h 07m
Frontier
Deal found 4/20![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 4/23. 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.
Wed 6/106:00 am
MDW
- DEN
1 stop8h 59m
Frontier
Deal found 4/23![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 4/21. 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.
Sun 5/244:05 pm
ORD
- DEN
1 stop8h 53m
Frontier
Deal found 4/21![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 4/20. 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.
Mon 5/46:20 am
MDW
- DEN
1 stop10h 25m
Frontier
Deal found 4/20![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 4/21. 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.
Tue 6/2312:31 pm
ORD
- DEN
1 stop6h 06m
Frontier
Deal found 4/21![Frontier logo]()
$95
This Southwest deal was found by Cheapflights users on 4/23. 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 6/312:20 pm
MDW
- DEN
1 stop6h 00m
Southwest
Deal found 4/23![Southwest logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 6/69:20 am
ORD
- DEN
1 stop11h 11m
Frontier
Deal found 4/23![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Sun 5/101:59 pm
ORD
- DEN
1 stop9h 25m
Frontier
Deal found 4/20![Frontier logo]()
$98
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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $160 (Kiwi.com) |
One-way from | $90 (Expedia) |
Popular in | March |
Cheapest in | September |
Average price | $264 |
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 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
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Mon 9/28
8:45 pm-10:20 pm
Nonstop2h 35m
Denver Intl
Wed 9/30
1:55 pm-7:25 pm
1 stop4h 30m
$196
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Wed 9/2
11:10 am-3:00 pm
1 stop4h 50m
Denver Intl
Sat 9/5
11:10 am-5:10 pm
1 stop5h 00m
$201
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Sat 6/6
1:59 pm-8:15 pm
1 stop7h 16m
Denver Intl
Tue 6/9
6:05 am-12:36 pm
1 stop5h 31m
$211
Quickest round-trip
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 6/9
5:30 am-7:05 am
Nonstop2h 35m
Denver Intl
Sat 6/13
5:15 am-8:35 am
Nonstop2h 20m
$212
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 6/5
9:25 pm-11:05 pm
Nonstop2h 40m
Denver Intl
Tue 6/9
10:25 am-5:00 pm
2 stops5h 35m
$216
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 6/5
6:36 pm-10:58 pm
1 stop5h 22m
Denver Intl
Wed 6/10
2:15 pm-10:17 pm
1 stop7h 02m
$229
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Tue 5/19
8:50 pm-10:35 pm
Nonstop2h 45m
Denver Intl
Wed 5/27
6:35 am-9:55 am
Nonstop2h 20m
$241
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Fri 6/5
6:36 pm-10:58 pm
1 stop5h 22m
Denver Intl
Mon 6/8
12:12 pm-6:18 pm
1 stop5h 06m
$243
ChicagoDenver
ORD - DEN
ORDDEN
Chicago O'Hare Intl
Fri 5/29
4:15 pm-11:45 pm
1 stop8h 30m
Denver Intl
Mon 6/1
5:20 am-12:50 pm
1 stop6h 30m
$244
ChicagoDenver
MDW - DEN
MDWDEN
Chicago Midway
Thu 6/4
5:15 am-6:50 am
Nonstop2h 35m
Denver Intl
Thu 6/11
5:55 am-9:20 am
Nonstop2h 25m
$246
Showing 1-10 of 46 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 April 24, 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 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.
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 24, 2026.
The most flights from CHI to BK9 are scheduled on a Thursday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 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 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.
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Breckenridge. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Breckenridge
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Complete your trip
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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 April 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 April 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 April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$152 | Average$336 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$153 | Average$306 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$160 | Average$390 | FlexibilityNo cancel fee | On-time69% |