$102+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 14 — Aug 211
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 Thursday or Friday and return on a Wednesday
Cheap flight deals from Breckenridge to Chicago
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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 15, 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 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Fri 8/79:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/13![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Tue 10/132:46 pm
ORD
- DEN
1 stop10h 07m
Frontier
Deal found 7/14![Frontier logo]()
$176
This Trip.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Sun 11/110:40 pm
ORD
- DEN
Nonstop2h 49m
Frontier
Deal found 7/14![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Fri 9/42:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/14![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/76:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Sun 10/1111:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Deal found 7/10![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/1512:25 pm
DEN
- MDW
1 stop6h 50m
Southwest
Tue 8/181:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$180
This Frontier deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 8/129:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/11![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/78:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 8/196:40 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/10![Southwest logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 8/109:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/13![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/138:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 8/156:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/10![Southwest logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 8/179:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/15![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 9/105:56 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Wed 9/1610:40 pm
ORD
- DEN
Nonstop2h 49m
Frontier
Deal found 7/11![Frontier logo]()
$184
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 15, 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 15, 2026.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/78:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 8/186:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/10![Southwest logo]()
$181
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/196:05 am
DEN
- ORD
1 stop6h 03m
Delta
Wed 8/265:20 pm
ORD
- DEN
1 stop6h 28m
Delta
Deal found 7/10![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/69:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Mon 8/106:00 am
ORD
- DEN
Nonstop2h 42m
United Airlines
Deal found 7/11![United Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/2712:47 pm
DEN
- RFD
1 stop6h 58m
Multiple Airlines
Sun 8/303:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/78:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 8/199:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/10![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/126:05 am
DEN
- ORD
1 stop5h 53m
Delta
Thu 9/175:10 pm
ORD
- DEN
1 stop5h 23m
Delta
Deal found 7/10![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Mon 10/1210:00 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 7/9![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/2210:30 am
DEN
- ORD
1 stop6h 55m
Delta
Mon 10/2612:33 pm
ORD
- DEN
1 stop4h 16m
Delta
Deal found 7/10![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/226:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/248:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/11![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/196:05 am
DEN
- ORD
1 stop6h 03m
Delta
Mon 8/246:00 am
ORD
- DEN
1 stop7h 08m
Delta
Deal found 7/10![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:30 am
DEN
- RFD
2 stops13h 09m
Multiple Airlines
Sun 9/273:53 pm
RFD
- DEN
1 stop22h 40m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$240
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 8/196:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/14![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/196:05 am
DEN
- MDW
1 stop5h 34m
Delta
Wed 8/196:42 pm
MDW
- DEN
1 stop5h 06m
Delta
Deal found 7/10![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/69:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Thu 8/135:55 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 7/9![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Thu 9/36:45 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/14![Southwest logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/257:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Sun 9/273:53 pm
RFD
- DEN
1 stop22h 40m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$252
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/812:25 pm
DEN
- MDW
1 stop6h 50m
Southwest
Sat 8/1510:10 am
MDW
- DEN
1 stop4h 20m
Southwest
Deal found 7/10![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/1912:59 am
DEN
- ORD
1 stop5h 57m
Delta
Fri 8/215:20 pm
ORD
- DEN
1 stop6h 28m
Delta
Deal found 7/10![Delta logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/208:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/239:35 pm
RFD
- DEN
1 stop7h 13m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:10 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Sun 9/277:00 am
ORD
- DEN
Nonstop2h 52m
United Airlines
Deal found 7/13![United Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:05 am
DEN
- ORD
1 stop6h 03m
Delta
Fri 8/145:20 pm
ORD
- DEN
1 stop6h 28m
Delta
Deal found 7/9![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Tue 8/118:50 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:01 am
DEN
- RFD
1 stop23h 30m
Multiple Airlines
Thu 8/1311:37 am
RFD
- DEN
2 stops20h 55m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Thu 10/19:20 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/14![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:30 am
DEN
- ORD
1 stop4h 54m
Delta
Mon 11/27:10 am
ORD
- DEN
1 stop7h 58m
Delta
Deal found 7/13![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/1511:20 am
DEN
- MDW
1 stop4h 55m
Southwest
Tue 8/189:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/11![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:04 am
DEN
- ORD
1 stop5h 37m
Delta
Wed 9/911:17 am
ORD
- DEN
1 stop7h 05m
Delta
Deal found 7/13![Delta logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Sun 9/139:29 pm
RFD
- DEN
1 stop7h 23m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:31 am
DEN
- RFD
1 stop5h 32m
Multiple Airlines
Sun 9/69:29 pm
RFD
- DEN
1 stop7h 19m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:45 pm
DEN
- RFD
1 stop18h 26m
Multiple Airlines
Sun 9/203:53 pm
RFD
- DEN
1 stop6h 56m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$334
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated July 15, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated July 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Fri 8/79:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/13![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Sun 8/99:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/14![Frontier logo]()
$184
This Frontier deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/54:25 pm
DEN
- ORD
1 stop12h 12m
Frontier
Wed 8/129:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/13![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 8/109:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/13![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/78:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 8/196:40 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/10![Southwest logo]()
$181
This Frontier deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 8/129:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/11![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:00 am
DEN
- ORD
1 stop8h 53m
Frontier
Thu 8/202:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/15![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/138:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 8/156:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/10![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/1512:25 pm
DEN
- MDW
1 stop6h 50m
Southwest
Tue 8/181:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 8/179:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/15![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/209:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Thu 8/279:20 am
ORD
- DEN
1 stop14h 35m
Frontier
Deal found 7/10![Frontier logo]()
$185
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Fri 9/42:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/14![Frontier logo]()
$179
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 15, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated July 15, 2026.
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fri 8/75:44 pm
DEN
- ORD
Nonstop3h 01m
American Airlines
Deal found 7/9![American Airlines logo]()
$102
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/98:55 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/10![Southwest logo]()
$102
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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.
Tue 8/49:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 7/11![United Airlines logo]()
$103
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:50 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/13![Southwest logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:00 am
DEN
- ORD
1 stop16h 33m
Frontier
Deal found 7/14![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/411:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 7/11![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:59 pm
DEN
- ORD
1 stop7h 03m
Frontier
Deal found 7/12![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/127:00 am
DEN
- MDW
1 stop28h 07m
Frontier
Deal found 7/10![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/128:01 am
DEN
- RFD
1 stop23h 10m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 10/1211:48 pm
DEN
- ORD
1 stop7h 27m
Frontier
Deal found 7/11![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:48 pm
DEN
- RFD
1 stop13h 31m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$107
This Expedia deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Wed 8/1211:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 7/10![Frontier logo]()
$107
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 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (Kiwi.com) |
One-way from | $102 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $284 |
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 15, 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 - MDW
DENMDW
Denver Intl
Fri 8/7
8:25 pm-11:45 pm
Nonstop2h 20m
Chicago Midway
Tue 8/18
6:00 pm-7:40 pm
Nonstop2h 40m
$181
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 8/7
8:25 pm-11:45 pm
Nonstop2h 20m
Chicago Midway
Wed 8/19
9:00 am-12:55 pm
1 stop4h 55m
$187
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 8/19
6:05 am-1:08 pm
1 stop6h 03m
Chicago O'Hare Intl
Wed 8/26
5:20 pm-10:48 pm
1 stop6h 28m
$197
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 9/12
6:05 am-12:58 pm
1 stop5h 53m
Chicago O'Hare Intl
Thu 9/17
5:10 pm-9:33 pm
1 stop5h 23m
$197
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 10/22
10:30 am-6:25 pm
1 stop6h 55m
Chicago O'Hare Intl
Mon 10/26
12:33 pm-3:49 pm
1 stop4h 16m
$197
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 8/19
6:05 am-1:08 pm
1 stop6h 03m
Chicago O'Hare Intl
Mon 8/24
6:00 am-12:08 pm
1 stop7h 08m
$197
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 8/19
6:05 am-12:39 pm
1 stop5h 34m
Chicago Midway
Wed 8/19
6:42 pm-10:48 pm
1 stop5h 06m
$197
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 8/6
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Mon 8/10
6:00 am-7:42 am
Nonstop2h 42m
$205
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 8/22
6:00 am-9:20 am
Nonstop2h 20m
Chicago Midway
Mon 8/24
8:15 pm-9:50 pm
Nonstop2h 35m
$205
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 8/12
6:30 am-9:50 am
Nonstop2h 20m
Chicago Midway
Wed 8/19
6:00 pm-7:40 pm
Nonstop2h 40m
$205
Showing 1-10 of 60 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-MDW
DEN-RFD
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-MDW
DEN-RFD
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 15, 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 15, 2026.
The most flights from BK9 to CHI are scheduled on a Monday (84 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Breckenridge to Chicago?
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 11, 2026.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Saturday afternoons 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 15, 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.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
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 15, 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 15, 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$76 | Average$193 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$337 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$168 | Average$388 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$426 | FlexibilityNo cancel fee | On-time69% |