$89+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Apr 16 — Apr 231
Round-trip
1 adult, Economy
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Find cheap flights from Breckenridge to Chicago with Cheapflights
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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 August or September, booked 79 days in advance, depart on a Thursday or Friday and return on a Saturday
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 März 17, 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 März 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Fr 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mi 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Deal found 3/16![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Fr 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Di 3/313:52 pm
ORD
- DEN
1 stop8h 21m
Frontier
Deal found 3/17![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 3/13. 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.
Di 7/149:59 am
DEN
- ORD
Nonstop2h 38m
Frontier
Sa 7/187:05 am
ORD
- DEN
Nonstop2h 57m
Frontier
Deal found 3/13![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Mo 4/1310:30 pm
DEN
- ORD
1 stop6h 50m
Multiple Airlines
Mo 4/209:44 pm
ORD
- DEN
1 stop13h 40m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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.
Do 5/146:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
So 5/175:25 am
ORD
- DEN
1 stop27h 41m
Frontier
Deal found 3/13![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/238:00 am
DEN
- MDW
1 stop13h 22m
Frontier
Mo 4/271:35 pm
MDW
- DEN
1 stop21h 08m
Frontier
Deal found 3/12![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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.
Do 4/2310:29 pm
DEN
- ORD
1 stop30h 21m
Frontier
Di 4/288:58 pm
ORD
- DEN
1 stop8h 01m
Frontier
Deal found 3/13![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Mo 4/139:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Mi 4/158:25 am
ORD
- DEN
1 stop9h 51m
Frontier
Deal found 3/17![Frontier logo]()
$180
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/291:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Do 4/308:25 am
MDW
- DEN
1 stop9h 28m
Frontier
Deal found 3/13![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Fr 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Fr 4/32:29 pm
ORD
- DEN
Nonstop3h 20m
Frontier
Deal found 3/16![Frontier logo]()
$181
This Booking.com deal was found by Cheapflights users on 3/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Mo 4/135:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 3/13![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 3/12. 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.
Fr 5/157:00 am
DEN
- ORD
1 stop7h 43m
Frontier
Di 5/199:42 pm
ORD
- DEN
Nonstop3h 10m
Frontier
Deal found 3/12![Frontier logo]()
$182
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 März 17, 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 März 17, 2026.
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Di 4/76:00 am
DEN
- ORD
Nonstop2h 37m
United Airlines
Mi 4/88:11 pm
ORD
- DEN
Nonstop2h 59m
United Airlines
Deal found 3/17![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Di 4/146:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Di 4/218:50 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 3/16![Southwest logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Fr 5/159:03 am
DEN
- RFD
1 stop9h 42m
Multiple Airlines
Mo 5/188:35 pm
RFD
- DEN
1 stop18h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/156:00 am
DEN
- ORD
Nonstop2h 37m
United Airlines
Fr 4/1710:04 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 3/12![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/112:45 pm
DEN
- MDW
1 stop5h 20m
Southwest
Mo 4/136:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/12![Southwest logo]()
$211
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Di 4/76:00 am
DEN
- ORD
Nonstop2h 37m
United Airlines
Sa 4/115:45 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 3/17![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/145:55 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Sa 4/185:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/15![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Mi 5/276:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sa 5/3010:30 am
MDW
- DEN
1 stop4h 45m
Southwest
Deal found 3/16![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Di 4/76:15 am
DEN
- ORD
1 stop5h 35m
Southwest
Mi 4/811:55 am
ORD
- DEN
2 stops8h 30m
Southwest
Deal found 3/17![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 3/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 6/119:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
So 6/145:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 3/15![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 3/14. 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.
Fr 5/295:35 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Mo 6/16:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/14![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sa 4/185:30 am
DEN
- MDW
1 stop6h 40m
Southwest
Sa 4/182:15 pm
MDW
- DEN
1 stop5h 45m
Southwest
Deal found 3/14![Southwest logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Do 4/99:10 am
DEN
- RFD
2 stops23h 44m
Multiple Airlines
Mo 4/138:35 pm
RFD
- DEN
1 stop14h 08m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/188:10 pm
DEN
- ORD
2 stops15h 40m
Southwest
Mo 4/202:40 pm
ORD
- DEN
2 stops10h 05m
Southwest
Deal found 3/12![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 6/47:05 pm
DEN
- MDW
1 stop4h 55m
Southwest
Di 6/912:05 pm
MDW
- DEN
1 stop3h 50m
Southwest
Deal found 3/15![Southwest logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Sa 6/1310:29 pm
DEN
- RFD
1 stop12h 54m
Multiple Airlines
Sa 6/271:04 pm
RFD
- DEN
1 stop21h 13m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/173:05 pm
DEN
- MDW
1 stop4h 25m
Southwest
Mo 4/209:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/15![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fr 5/88:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mo 5/114:05 pm
MDW
- DEN
1 stop4h 15m
Southwest
Deal found 3/13![Southwest logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Mi 3/2512:54 pm
DEN
- RFD
2 stops19h 53m
Multiple Airlines
Sa 3/289:55 pm
RFD
- DEN
1 stop12h 49m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Do 6/47:05 pm
DEN
- MDW
1 stop4h 55m
Southwest
So 6/75:25 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 3/16![Southwest logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Mi 4/17:05 pm
DEN
- RFD
2 stops13h 42m
Multiple Airlines
Sa 4/49:11 pm
RFD
- DEN
1 stop12h 47m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$521
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/265:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
So 5/39:55 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/12![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 3/14. 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.
Do 4/96:05 am
DEN
- ORD
1 stop6h 10m
Southwest
Sa 4/112:05 pm
ORD
- DEN
2 stops9h 15m
Southwest
Deal found 3/14![Southwest logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Fr 4/35:53 pm
DEN
- RFD
1 stop15h 01m
Multiple Airlines
So 4/512:45 pm
RFD
- DEN
1 stop16h 14m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$545
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sa 4/187:00 am
DEN
- ORD
1 stop6h 30m
Southwest
Sa 4/184:15 pm
ORD
- DEN
1 stop7h 00m
Southwest
Deal found 3/14![Southwest logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Sa 3/2810:30 pm
DEN
- RFD
1 stop12h 25m
Multiple Airlines
Do 4/910:37 am
RFD
- DEN
2 stops22h 32m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$549
This Southwest deal was found by Cheapflights users on 3/14. 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.
Do 4/166:05 am
DEN
- ORD
2 stops8h 25m
Southwest
Mo 4/204:15 pm
ORD
- DEN
2 stops8h 10m
Southwest
Deal found 3/14![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/17:05 pm
DEN
- RFD
2 stops13h 42m
Multiple Airlines
Mi 4/85:46 pm
RFD
- DEN
1 stop15h 35m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$566
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fr 5/83:00 pm
DEN
- ORD
1 stop7h 55m
Southwest
Mo 5/113:45 pm
ORD
- DEN
2 stops9h 00m
Southwest
Deal found 3/13![Southwest logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Sa 3/2810:30 pm
DEN
- RFD
1 stop12h 25m
Multiple Airlines
So 4/1210:37 am
RFD
- DEN
2 stops22h 32m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$569
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated März 17, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated März 17, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/12. 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.
Do 3/266:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Di 3/318:55 pm
ORD
- DEN
1 stop8h 04m
Frontier
Deal found 3/12![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Do 3/266:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Fr 4/32:29 pm
ORD
- DEN
Nonstop3h 20m
Frontier
Deal found 3/13![Frontier logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Fr 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mi 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Deal found 3/16![Frontier logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Fr 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Di 3/313:52 pm
ORD
- DEN
1 stop8h 21m
Frontier
Deal found 3/17![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Fr 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Fr 4/32:29 pm
ORD
- DEN
Nonstop3h 20m
Frontier
Deal found 3/16![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Mi 4/110:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Mo 4/62:29 pm
ORD
- DEN
Nonstop3h 11m
Frontier
Deal found 3/17![Frontier logo]()
$183
This Booking.com deal was found by Cheapflights users on 3/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Mo 4/135:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 3/13![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Mo 4/1310:30 pm
DEN
- ORD
1 stop6h 50m
Multiple Airlines
Mo 4/209:44 pm
ORD
- DEN
1 stop13h 40m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Mo 4/139:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Mi 4/158:25 am
ORD
- DEN
1 stop9h 51m
Frontier
Deal found 3/17![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/238:00 am
DEN
- MDW
1 stop13h 22m
Frontier
Mo 4/271:35 pm
MDW
- DEN
1 stop21h 08m
Frontier
Deal found 3/12![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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.
Do 4/236:00 am
DEN
- ORD
1 stop29h 13m
Frontier
Mo 4/277:21 pm
ORD
- DEN
1 stop25h 28m
Frontier
Deal found 3/13![Frontier logo]()
$179
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/291:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Do 4/308:25 am
MDW
- DEN
1 stop9h 28m
Frontier
Deal found 3/13![Frontier logo]()
$180
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 März 17, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated März 17, 2026.
This Super.com deal was found by Cheapflights users on 3/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Deal found 3/12![Frontier logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Mo 5/1111:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 3/17![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Sa 6/65:05 am
DEN
- MDW
1 stop8h 07m
Frontier
Deal found 3/17![Frontier logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Sa 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/16![Frontier logo]()
$91
This Flightnetwork deal was found by Cheapflights users on 3/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/206:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/12![Frontier logo]()
$92
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/86:00 am
DEN
- ORD
Nonstop2h 37m
United Airlines
Deal found 3/12![United Airlines logo]()
$93
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/226:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/12![Southwest logo]()
$93
This Super.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
So 5/36:00 am
DEN
- ORD
1 stop23h 20m
Frontier
Deal found 3/16![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Di 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Deal found 3/16![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 3/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 3/309:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/12![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” 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.
Fr 4/173:32 pm
DEN
- MDW
1 stop23h 28m
Frontier
Deal found 3/16![Frontier logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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.
So 5/1711:56 pm
DEN
- ORD
1 stop22h 17m
Frontier
Deal found 3/13![Frontier logo]()
$96
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 März 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (Cheapflightsfares) |
One-way from | $89 (Super.com) |
Popular in | March |
Cheapest in | August |
Average price | $275 |
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 März 17, 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 - ORD
DENORD
Denver Intl
Di 4/7
6:00 am-9:37 am
Nonstop2h 37m
Chicago O'Hare Intl
Mi 4/8
8:11 pm-10:10 pm
Nonstop2h 59m
$201
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Di 4/14
6:35 am-9:55 am
Nonstop2h 20m
Chicago Midway
Di 4/21
8:50 pm-10:35 pm
Nonstop2h 45m
$201
DenverChicago
DEN - ORD
DENORD
Denver Intl
Mi 4/15
6:00 am-9:37 am
Nonstop2h 37m
Chicago O'Hare Intl
Fr 4/17
10:04 pm-11:59 pm
Nonstop2h 55m
$211
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sa 4/11
2:45 pm-9:05 pm
1 stop5h 20m
Chicago Midway
Mo 4/13
6:00 am-7:40 am
Nonstop2h 40m
$211
DenverChicago
DEN - ORD
DENORD
Denver Intl
Di 4/7
6:00 am-9:37 am
Nonstop2h 37m
Chicago O'Hare Intl
Sa 4/11
5:45 pm-7:40 pm
Nonstop2h 55m
$211
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Di 4/14
5:55 pm-9:30 pm
Nonstop2h 35m
Chicago Midway
Sa 4/18
5:30 pm-7:10 pm
Nonstop2h 40m
$215
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mi 5/27
6:35 am-9:55 am
Nonstop2h 20m
Chicago Midway
Sa 5/30
10:30 am-2:15 pm
1 stop4h 45m
$218
DenverChicago
DEN - ORD
DENORD
Denver Intl
Di 4/7
6:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Mi 4/8
11:55 am-7:25 pm
2 stops8h 30m
$226
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fr 5/29
5:35 pm-9:05 pm
Nonstop2h 30m
Chicago Midway
Mo 6/1
6:00 am-7:40 am
Nonstop2h 40m
$233
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sa 4/18
5:30 am-1:10 pm
1 stop6h 40m
Chicago Midway
Sa 4/18
2:15 pm-7:00 pm
1 stop5h 45m
$235
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
How far ahead should I book a flight from Breckenridge to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Breckenridge to Chicago. Price data was last updated on March 13, 2026.
The price you pay for your flight from Breckenridge to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Breckenridge to Chicago?
Currently, April is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $81). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $140). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from 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 März 17, 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 63% versus a flight at noon.
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 March 14, 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 März 17, 2026.
The most flights from BK9 to CHI are scheduled on a Friday (65 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (40 on average).
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 März 17, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes
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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 März 17, 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 März 17, 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 März 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$292 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$380 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$161 | Average$396 | FlexibilityNo cancel fee | On-time69% |