$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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 31 — Sep 71
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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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 August 1, 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 August 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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
Thu 9/35:46 pm
ORD
- DEN
1 stop20h 34m
Frontier
Deal found 7/30![Frontier logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/176:13 pm
DEN
- ORD
1 stop26h 26m
Frontier
Sun 9/206:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/31![Frontier logo]()
$170
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:48 pm
DEN
- MDW
1 stop10h 10m
Frontier
Sat 10/246:40 am
MDW
- DEN
1 stop8h 20m
Frontier
Deal found 7/31![Frontier logo]()
$170
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
Tue 9/12:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/27![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/1611:48 pm
DEN
- ORD
1 stop7h 27m
Frontier
Mon 10/1911:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Deal found 7/31![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/229:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Sat 8/292:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/30![Frontier logo]()
$173
This FlightHub deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Sat 8/2911:45 am
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 8/1![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/269:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Wed 8/269:20 pm
ORD
- DEN
1 stop13h 43m
Frontier
Deal found 7/30![Frontier logo]()
$174
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Thu 9/1010:44 am
DEN
- MDW
1 stop12h 00m
Frontier
Mon 9/1412:54 pm
MDW
- DEN
1 stop9h 55m
Frontier
Deal found 7/30![Frontier logo]()
$174
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 9/188:55 pm
DEN
- ORD
Nonstop2h 28m
Frontier
Sun 9/206:30 am
ORD
- DEN
Nonstop2h 45m
Frontier
Deal found 7/27![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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
Mon 8/312:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 8/1![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:59 pm
DEN
- MDW
1 stop9h 59m
Frontier
Thu 11/127:25 am
MDW
- DEN
1 stop7h 35m
Frontier
Deal found 7/30![Frontier logo]()
$176
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 August 1, 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 August 1, 2026.
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 Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/63:53 pm
RFD
- DEN
2 stops36h 55m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$218
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.
Tue 10/136:10 am
DEN
- ORD
1 stop5h 49m
Delta
Sat 10/1711:12 am
ORD
- DEN
1 stop6h 56m
Delta
Deal found 7/27![Delta logo]()
$233
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 7/27. 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 10/128:55 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 10/176:35 am
MDW
- DEN
1 stop5h 00m
Southwest
Deal found 7/27![Southwest logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/206:10 am
DEN
- RFD
1 stop13h 35m
Multiple Airlines
Sun 8/233:59 pm
RFD
- DEN
1 stop24h 02m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$240
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:15 am
DEN
- MDW
1 stop3h 50m
Southwest
Wed 9/168:50 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/29![Southwest logo]()
$219
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/187:10 pm
DEN
- ORD
Nonstop2h 35m
United Airlines
Mon 9/215:55 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 7/31![United Airlines logo]()
$247
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 Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Sat 9/196:50 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/29![Southwest logo]()
$219
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 9/2210:47 pm
DEN
- RFD
1 stop13h 32m
Multiple Airlines
Sun 9/273:53 pm
RFD
- DEN
1 stop26h 23m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$245
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 7/31. Clicking the “Pick Dates” 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 9/53:05 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 9/912:00 pm
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/31![Southwest logo]()
$225
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.
Mon 8/177:10 pm
DEN
- ORD
Nonstop2h 36m
United Airlines
Mon 8/247:50 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 7/27![United Airlines logo]()
$293
This Kiwi.com 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 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 9/139:29 pm
RFD
- DEN
2 stops21h 30m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$268
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:40 am
DEN
- MDW
1 stop4h 25m
Southwest
Mon 9/284:10 pm
MDW
- DEN
1 stop4h 40m
Southwest
Deal found 7/29![Southwest logo]()
$228
This Kiwi.com 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 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
Sun 9/209:29 pm
RFD
- DEN
2 stops21h 30m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Thu 10/15:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 7/31![United Airlines logo]()
$312
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 8/218:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/247:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/27![Southwest logo]()
$235
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.
Sat 9/54:09 pm
DEN
- ORD
1 stop4h 38m
Delta
Tue 9/811:17 am
ORD
- DEN
1 stop7h 04m
Delta
Deal found 7/28![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Sun 8/165:48 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Sat 8/2210:00 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 7/30![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/286:30 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Thu 10/19:20 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/31![Southwest logo]()
$237
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 9/257:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Mon 9/288:44 pm
RFD
- DEN
1 stop13h 59m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$296
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.
Mon 9/76:00 am
DEN
- ORD
Nonstop2h 43m
United Airlines
Mon 9/710:00 pm
ORD
- DEN
Nonstop2h 53m
United Airlines
Deal found 7/28![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/2611:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Mon 8/317:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/31![Southwest logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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
Mon 9/148:44 pm
RFD
- DEN
1 stop13h 59m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:35 am
DEN
- ORD
Nonstop2h 44m
United Airlines
Wed 8/267:50 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 7/31![United Airlines logo]()
$317
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 8/318:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Fri 9/48:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/27![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/226:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 9/284:10 pm
MDW
- DEN
1 stop4h 40m
Southwest
Deal found 7/31![Southwest logo]()
$247
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Sun 9/207:00 am
ORD
- DEN
Nonstop2h 47m
United Airlines
Deal found 7/29![United Airlines logo]()
$334
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated August 1, 2026 and is based on user searches.
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.
Tue 8/115:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 8/192:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/29![Frontier logo]()
$179
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.
Tue 8/115:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/182:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 7/27![Frontier logo]()
$199
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:09 am
DEN
- MDW
1 stop9h 22m
Frontier
Fri 8/289:26 pm
MDW
- DEN
1 stop10h 02m
Frontier
Deal found 7/30![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:09 am
DEN
- MDW
1 stop9h 22m
Frontier
Sun 8/236:05 am
MDW
- DEN
1 stop8h 56m
Frontier
Deal found 7/30![Frontier logo]()
$207
This FlightHub deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Sat 8/2911:45 am
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 8/1![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Sun 8/2311:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Thu 8/279:26 pm
MDW
- DEN
1 stop10h 02m
Frontier
Deal found 7/30![Frontier logo]()
$197
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2511:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Sun 8/306:05 am
MDW
- DEN
1 stop8h 56m
Frontier
Deal found 7/30![Frontier logo]()
$177
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:43 am
DEN
- MDW
1 stop11h 04m
Frontier
Wed 8/2611:50 am
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 7/29![Frontier logo]()
$192
This Justfly.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Fri 8/289:26 pm
MDW
- DEN
1 stop10h 02m
Frontier
Deal found 8/1![Frontier logo]()
$183
This Kiwi.com 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 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 7/29![Multiple Airlines logo]()
$180
This Priceline deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Thu 8/2711:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Thu 9/311:50 am
MDW
- DEN
1 stop11h 15m
Frontier
Deal found 7/30![Frontier logo]()
$201
This Priceline deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Fri 8/2810:09 am
DEN
- MDW
1 stop9h 22m
Frontier
Sun 8/306:05 am
MDW
- DEN
1 stop8h 56m
Frontier
Deal found 7/30![Frontier logo]()
$187
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 August 1, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
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.
Wed 8/199:06 pm
DEN
- ORD
1 stop26h 43m
Frontier
Deal found 7/27![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Mon 11/210:56 am
DEN
- MDW
1 stop9h 57m
Frontier
Deal found 7/30![Frontier logo]()
$103
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.
Sat 8/227:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 7/28![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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.
Sun 11/111:59 pm
DEN
- MDW
1 stop9h 59m
Frontier
Deal found 7/30![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 7/27. 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.
Fri 9/119:16 pm
DEN
- ORD
1 stop16h 01m
Frontier
Deal found 7/27![Frontier logo]()
$106
This United Airlines 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 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 7/29![United Airlines logo]()
$107
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/29![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 Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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
Deal found 7/30![Multiple Airlines 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
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 August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $169 (Cheapflightsfares) |
One-way from | $103 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $230 |
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 August 1, 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
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 - RFD
DENRFD
Denver Intl
Thu 9/3
8:31 am-3:03 pm
1 stop5h 32m
Chicago Greater Rockford
Sun 9/6
3:53 pm-3:48 am
2 stops36h 55m
$218
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 10/12
8:55 pm-12:15 am
Nonstop2h 20m
Chicago Midway
Sat 10/17
6:35 am-10:35 am
1 stop5h 00m
$219
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 9/16
11:15 am-4:05 pm
1 stop3h 50m
Chicago Midway
Wed 9/16
8:50 pm-10:30 pm
Nonstop2h 40m
$219
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 9/12
11:10 am-5:10 pm
1 stop5h 00m
Chicago Midway
Sat 9/19
6:50 am-8:20 am
Nonstop2h 30m
$219
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 9/5
3:05 pm-6:30 pm
Nonstop2h 25m
Chicago Midway
Wed 9/9
12:00 pm-1:30 pm
Nonstop2h 30m
$225
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 9/26
11:40 am-5:05 pm
1 stop4h 25m
Chicago Midway
Mon 9/28
4:10 pm-7:50 pm
1 stop4h 40m
$228
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 10/13
6:10 am-12:59 pm
1 stop5h 49m
Chicago O'Hare Intl
Sat 10/17
11:12 am-5:08 pm
1 stop6h 56m
$233
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 8/21
8:25 pm-11:45 pm
Nonstop2h 20m
Chicago Midway
Mon 8/24
7:35 pm-9:10 pm
Nonstop2h 35m
$235
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 9/28
6:30 pm-10:05 pm
Nonstop2h 35m
Chicago Midway
Thu 10/1
9:20 pm-11:00 pm
Nonstop2h 40m
$237
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-MDW
DEN-RFD
DEN-ORD
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-MDW
DEN-RFD
DEN-ORD
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 August 1, 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 August 1, 2026.
The most flights from BK9 to CHI are scheduled on a Thursday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 August.The cheapest round-trip price found within the last 5 days was $169 on Frontier (Aug 27-Sep 3).
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 August 1, 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
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
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
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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 August 1, 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 August 1, 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 August 1, 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% |