$103+ Cheap flights from Breckenridge, CO to Chicago (CHI)
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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 28 — Sep 41
Round-trip
1 adult, Economy
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Find cheap flights from Breckenridge to Chicago 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 Breckenridge to Chicago are usually found in January or September, booked 79 days in advance, depart on a Friday or Thursday and return on a Wednesday
Cheap flight deals from Breckenridge to Chicago
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Last-minute
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Cheapest flights from Breckenridge to ChicagoExplore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2026.
Explore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2026.
This Kissandfly.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:55 pm
DEN
- ORD
Nonstop2h 28m
Frontier
Thu 9/1710:30 pm
ORD
- DEN
Nonstop2h 47m
Frontier
Deal found 7/27![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/279:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Sat 8/292:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/26![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/135:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/182:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/24![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/279:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 9/12:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/27![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/39:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 9/156:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/28![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/188:55 pm
DEN
- ORD
Nonstop2h 28m
Frontier
Sun 9/206:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/26![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/176:09 am
DEN
- ORD
1 stop14h 30m
Frontier
Sat 9/196:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/27![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/209:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 8/252:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/26![Frontier logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/79:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Fri 9/116:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/24![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/148:55 pm
DEN
- ORD
Nonstop2h 28m
Frontier
Thu 9/178:55 pm
ORD
- DEN
1 stop16h 56m
Frontier
Deal found 7/29![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/226:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Sun 10/2511:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Deal found 7/28![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/278:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/303:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$180
Best flights from Breckenridge to ChicagoDiscover carefully curated flight deals from Breckenridge to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2026.
Discover carefully curated flight deals from Breckenridge to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/107:30 am
DEN
- RFD
1 stop12h 09m
Multiple Airlines
Sun 9/133:53 pm
RFD
- DEN
1 stop22h 40m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$204
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:50 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Mon 9/75:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 7/28![United Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/11:40 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 9/88:50 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/27![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
DEN
- ORD
1 stop6h 03m
Delta
Wed 9/26:44 pm
ORD
- DEN
1 stop5h 50m
Delta
Deal found 7/26![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/108:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Mon 9/147:00 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/28![Southwest logo]()
$213
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Sun 9/205:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 7/27![United Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/288:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 9/2910:20 am
MDW
- DEN
1 stop5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:19 am
DEN
- ORD
1 stop4h 58m
Delta
Fri 8/288:48 am
ORD
- DEN
1 stop5h 57m
Delta
Deal found 7/27![Delta logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/1710:47 pm
DEN
- RFD
1 stop18h 24m
Multiple Airlines
Sun 9/209:29 pm
RFD
- DEN
1 stop7h 23m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/272:20 pm
DEN
- MDW
1 stop4h 25m
Southwest
Thu 10/2911:50 am
MDW
- DEN
1 stop3h 50m
Southwest
Deal found 7/28![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/166:30 am
DEN
- ORD
1 stop5h 29m
Delta
Fri 9/185:10 pm
ORD
- DEN
1 stop5h 22m
Delta
Deal found 7/26![Delta logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/226:23 am
DEN
- RFD
1 stop12h 07m
Multiple Airlines
Sun 10/258:53 pm
RFD
- DEN
1 stop7h 59m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 12/46:05 am
DEN
- MDW
1 stop5h 30m
Delta
Tue 12/812:30 pm
MDW
- DEN
1 stop4h 29m
Delta
Deal found 7/28![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/256:30 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Wed 9/309:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/28![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/106:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Sat 10/171:30 pm
ORD
- DEN
Nonstop2h 47m
United Airlines
Deal found 7/24![United Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/1410:30 pm
DEN
- RFD
1 stop20h 43m
Multiple Airlines
Sun 10/189:33 pm
RFD
- DEN
1 stop7h 19m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:59 am
DEN
- ORD
1 stop5h 57m
Delta
Sun 8/306:00 am
ORD
- DEN
1 stop4h 59m
Delta
Deal found 7/28![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/43:55 pm
DEN
- MDW
1 stop4h 40m
Southwest
Sun 9/64:00 pm
MDW
- DEN
1 stop4h 25m
Southwest
Deal found 7/27![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/187:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Mon 9/218:44 pm
RFD
- DEN
1 stop13h 59m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/133:50 pm
DEN
- ORD
Nonstop2h 40m
United Airlines
Mon 8/1710:00 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 7/24![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/226:10 am
DEN
- ORD
1 stop5h 51m
Delta
Sun 10/252:00 pm
ORD
- DEN
1 stop8h 15m
Delta
Deal found 7/24![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/196:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 9/206:30 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/27![Southwest logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/2510:48 pm
DEN
- RFD
1 stop13h 35m
Multiple Airlines
Wed 9/22:09 pm
RFD
- DEN
2 stops19h 56m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/312:59 am
DEN
- ORD
1 stop5h 57m
Delta
Fri 9/45:20 pm
ORD
- DEN
1 stop6h 28m
Delta
Deal found 7/26![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:10 am
DEN
- MDW
Nonstop2h 25m
Southwest
Mon 9/213:15 pm
MDW
- DEN
1 stop5h 05m
Southwest
Deal found 7/27![Southwest logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/109:43 am
DEN
- RFD
1 stop9h 56m
Multiple Airlines
Mon 9/148:44 pm
RFD
- DEN
1 stop13h 59m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/256:30 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Mon 9/284:10 pm
MDW
- DEN
1 stop4h 40m
Southwest
Deal found 7/24![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/312:59 am
DEN
- ORD
1 stop5h 57m
Delta
Mon 9/76:59 am
ORD
- DEN
1 stop7h 46m
Delta
Deal found 7/25![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/315:00 am
DEN
- MDW
1 stop5h 00m
Southwest
Fri 9/48:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/27![Southwest logo]()
$254
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated July 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/135:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/182:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/24![Frontier logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/175:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 8/242:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/27![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/187:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Thu 8/202:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/26![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/187:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Wed 8/192:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/27![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/189:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Mon 8/242:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/24![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/209:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 8/252:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/26![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/209:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Wed 8/262:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/28![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/219:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 8/252:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/25![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/279:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Sat 8/292:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/26![Frontier logo]()
$171
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/279:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 9/12:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/27![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/278:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/303:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/289:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 9/12:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/26![Frontier logo]()
$184
One-way flights from Breckenridge to ChicagoSearch for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/269:06 pm
DEN
- ORD
1 stop26h 43m
Frontier
Deal found 7/26![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/58:31 am
DEN
- RFD
1 stop29h 32m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/187:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/26![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/69:21 pm
DEN
- ORD
1 stop26h 28m
Frontier
Deal found 7/27![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/119:16 pm
DEN
- ORD
1 stop16h 01m
Frontier
Deal found 7/26![Frontier logo]()
$106
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/277:10 pm
DEN
- ORD
Nonstop2h 35m
United Airlines
Deal found 7/28![United Airlines logo]()
$107
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/248:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/28![Southwest logo]()
$107
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/115:48 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Deal found 7/27![United Airlines logo]()
$108
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/114:55 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/28![Southwest logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/289:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/27![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/89:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Deal found 7/26![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/147:08 pm
DEN
- RFD
1 stop24h 05m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$111
Find flight deals from Breckenridge to Chicago
Keep the following information in mind while searching for Breckenridge to Chicago flight deals. Data was last updated July 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $170 (Kissandfly.com) |
One-way from | $103 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $317 |
Cheapflights Fare Finder
Customize your flight search to find flights from Breckenridge to Chicago 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 29, 2026.
Use the filters below to find and compare flights from Breckenridge to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DenverChicago
DEN - RFD
DENRFD
Denver Intl
Thu 9/10
7:30 am-8:39 pm
1 stop12h 09m
Chicago Greater Rockford
Sun 9/13
3:53 pm-1:33 pm
1 stop22h 40m
$204
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 9/5
2:50 pm-6:32 pm
Nonstop2h 42m
Chicago O'Hare Intl
Mon 9/7
5:00 am-6:39 am
Nonstop2h 39m
$213
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 9/1
1:40 pm-5:05 pm
Nonstop2h 25m
Chicago Midway
Tue 9/8
8:50 pm-10:30 pm
Nonstop2h 40m
$213
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 9/10
8:25 pm-11:50 pm
Nonstop2h 25m
Chicago Midway
Mon 9/14
7:00 am-8:30 am
Nonstop2h 30m
$213
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 9/28
8:25 pm-11:50 pm
Nonstop2h 25m
Chicago Midway
Tue 9/29
10:20 am-2:35 pm
1 stop5h 15m
$223
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 10/27
2:20 pm-7:45 pm
1 stop4h 25m
Chicago Midway
Thu 10/29
11:50 am-2:40 pm
1 stop3h 50m
$228
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 8/26
6:05 am-1:08 pm
1 stop6h 03m
Chicago O'Hare Intl
Wed 9/2
6:44 pm-11:34 pm
1 stop5h 50m
$233
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 9/25
6:30 pm-10:05 pm
Nonstop2h 35m
Chicago Midway
Wed 9/30
9:00 am-12:55 pm
1 stop4h 55m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 9/19
6:00 am-9:43 am
Nonstop2h 43m
Chicago O'Hare Intl
Sun 9/20
5:00 am-6:39 am
Nonstop2h 39m
$244
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 9/4
3:55 pm-9:35 pm
1 stop4h 40m
Chicago Midway
Sun 9/6
4:00 pm-7:25 pm
1 stop4h 25m
$251
Showing 1-10 of 59 resultsSorted by cheapest first
Best time to book a flight from Breckenridge to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Breckenridge with our price prediction graph.
DEN-ORD
DEN-RFD
DEN-MDW
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 Breckenridge to Chicago
BK9-CHI
DEN-ORD
DEN-RFD
DEN-MDW
What is the cheapest time of day to fly from BK9 to CHI?
Find hourly flight availability from Breckenridge to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2026.
When flying from Breckenridge to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 54% versus a flight at noon.
Weekly flight availability from Breckenridge to Chicago
Explore weekly flight availability from Breckenridge to Chicago. 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 29, 2026.
The most flights from BK9 to CHI are scheduled on a Monday (83 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 Breckenridge to Chicago?
Airfare is typical for this route at the moment.
Breckenridge to Chicago flights typically cost between $168 and $305 in September.The cheapest round-trip price found within the last 5 days was $170 on Frontier (Sep 10-Sep 17).
What is the cheapest day to fly from Breckenridge to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Breckenridge to Chicago. Price data was last updated on July 25, 2026.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 29, 2026.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Breckenridge to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Breckenridge to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 29, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Breckenridge to Chicago by cabin class
Find flights from Breckenridge to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Breckenridge and Chicago flights
Browse other Breckenridge and Chicago flight options. Last updated on July 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Breckenridge to Chicago
Discover the top 5 airlines that operate flights from Breckenridge to Chicago. 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$168 | Average$389 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$170 | Average$344 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$179 | Average$427 | FlexibilityNo cancel fee | On-time69% |