$88+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Jul 5 — Jul 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 August or January, booked 79 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Breckenridge to Chicago
Cheapest
Best
Last-minute
One-way
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 June 5, 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 June 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/146:30 am
DEN
- ORD
1 stop12h 23m
Frontier
Wed 7/221:50 pm
ORD
- DEN
1 stop9h 15m
Frontier
Deal found 6/3![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/275:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 8/299:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/4![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:30 pm
DEN
- ORD
1 stop6h 57m
Frontier
Sat 7/189:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$187
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Tue 7/79:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:42 pm
DEN
- ORD
1 stop11h 20m
Frontier
Mon 9/1411:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Deal found 6/2![Frontier logo]()
$189
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Thu 6/255:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 6/279:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/4![Frontier logo]()
$190
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/185:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 7/229:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/295:05 am
DEN
- MDW
1 stop8h 02m
Frontier
Tue 9/112:27 pm
MDW
- DEN
1 stop10h 49m
Frontier
Deal found 6/2![Frontier logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/2811:42 pm
DEN
- ORD
1 stop7h 21m
Frontier
Tue 9/19:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/3![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/111:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$193
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/35:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/2![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/1710:30 pm
DEN
- ORD
1 stop12h 27m
Frontier
Sat 9/1910:40 pm
ORD
- DEN
Nonstop2h 49m
Frontier
Deal found 6/3![Frontier logo]()
$195
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 June 5, 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 June 5, 2026.
This United Airlines deal was found by Cheapflights users on 6/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Tue 8/181:30 pm
ORD
- DEN
Nonstop2h 47m
United Airlines
Deal found 6/1![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 6/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:10 am
DEN
- ORD
1 stop4h 39m
Delta
Tue 10/136:00 am
ORD
- DEN
1 stop7h 03m
Delta
Deal found 6/1![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/710:15 am
DEN
- MDW
1 stop5h 40m
Southwest
Fri 7/105:05 am
MDW
- DEN
1 stop5h 15m
Southwest
Deal found 6/4![Southwest logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/207:23 am
DEN
- RFD
1 stop6h 46m
Multiple Airlines
Sun 8/239:35 pm
RFD
- DEN
1 stop12h 55m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/19:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sat 7/46:59 am
ORD
- DEN
Nonstop2h 50m
United Airlines
Deal found 6/4![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:30 am
DEN
- ORD
1 stop7h 10m
Delta
Sat 10/108:55 am
ORD
- DEN
1 stop6h 08m
Delta
Deal found 5/31![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 5/31. 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.
Sat 7/187:10 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Wed 7/299:50 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Deal found 5/31![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 5/31. 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.
Thu 8/209:00 am
DEN
- MDW
1 stop4h 35m
Southwest
Sun 8/239:15 am
MDW
- DEN
1 stop4h 40m
Southwest
Deal found 5/31![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/74:00 pm
DEN
- ORD
1 stop4h 34m
Delta
Tue 10/136:00 am
ORD
- DEN
1 stop7h 03m
Delta
Deal found 6/4![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/19:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sun 7/56:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 6/2![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/98:45 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 10/128:10 am
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/4![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:00 pm
DEN
- ORD
1 stop4h 34m
Delta
Mon 9/145:42 pm
ORD
- DEN
1 stop6h 43m
Delta
Deal found 5/31![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/277:23 am
DEN
- RFD
1 stop6h 46m
Multiple Airlines
Sun 8/303:59 pm
RFD
- DEN
1 stop23h 10m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 6/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:05 am
DEN
- MDW
1 stop3h 55m
Southwest
Tue 8/181:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 6/1![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/1211:15 am
DEN
- ORD
1 stop4h 33m
Delta
Sat 9/197:01 am
ORD
- DEN
1 stop7h 50m
Delta
Deal found 6/2![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/239:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sun 7/265:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 6/4![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/95:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Thu 7/912:05 pm
MDW
- DEN
1 stop5h 00m
Southwest
Deal found 6/2![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/712:55 am
DEN
- ORD
1 stop6h 05m
Delta
Tue 10/137:40 pm
ORD
- DEN
1 stop4h 19m
Delta
Deal found 6/4![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 5/31. 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.
Sat 10/106:10 am
DEN
- RFD
1 stop12h 58m
Multiple Airlines
Sun 10/119:33 pm
RFD
- DEN
1 stop12h 31m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:55 am
DEN
- MDW
1 stop6h 50m
Delta
Mon 10/129:30 am
MDW
- DEN
1 stop5h 33m
Delta
Deal found 6/4![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 6/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:05 pm
DEN
- MDW
1 stop4h 55m
Southwest
Sun 7/55:00 am
MDW
- DEN
1 stop5h 20m
Southwest
Deal found 6/1![Southwest logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 6/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:15 am
DEN
- RFD
1 stop9h 44m
Multiple Airlines
Thu 7/309:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 6/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:25 am
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 10/136:20 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 6/1![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/2610:26 am
DEN
- MDW
1 stop7h 07m
Delta
Fri 8/286:42 pm
MDW
- DEN
1 stop5h 06m
Delta
Deal found 6/3![Delta logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 5/31. 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.
Wed 7/159:15 am
DEN
- RFD
1 stop9h 44m
Multiple Airlines
Sun 7/199:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:05 am
DEN
- MDW
1 stop5h 34m
Delta
Sun 8/166:42 pm
MDW
- DEN
1 stop5h 06m
Delta
Deal found 5/31![Delta logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:17 pm
DEN
- RFD
2 stops22h 10m
Multiple Airlines
Sun 10/119:33 pm
RFD
- DEN
1 stop7h 19m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 6/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:59 am
DEN
- MDW
1 stop7h 18m
Delta
Sun 8/237:25 pm
MDW
- DEN
1 stop5h 09m
Delta
Deal found 6/1![Delta logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/17:43 am
DEN
- RFD
1 stop23h 46m
Multiple Airlines
Sun 7/59:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/412:12 pm
DEN
- MDW
1 stop4h 42m
Delta
Mon 7/137:06 pm
MDW
- DEN
1 stop5h 21m
Delta
Deal found 6/2![Delta logo]()
$285
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated June 5, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated June 5, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Thu 6/255:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 6/279:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/3![Frontier logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/275:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 7/19:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/4![Frontier logo]()
$195
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Tue 7/79:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/111:46 pm
DEN
- ORD
1 stop7h 17m
Frontier
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$193
This Southwest deal was found by Cheapflights users on 6/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:20 pm
DEN
- MDW
1 stop3h 45m
Southwest
Wed 7/89:05 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/1![Southwest logo]()
$223
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/35:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/2![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 7/139:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/3![Frontier logo]()
$192
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/76:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 7/149:05 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/2![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/85:05 am
DEN
- MDW
1 stop9h 45m
Frontier
Tue 7/146:05 am
MDW
- DEN
1 stop17h 00m
Frontier
Deal found 6/3![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/146:30 am
DEN
- ORD
1 stop12h 23m
Frontier
Wed 7/221:50 pm
ORD
- DEN
1 stop9h 15m
Frontier
Deal found 6/3![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/1412:30 pm
DEN
- ORD
1 stop6h 57m
Frontier
Sat 7/189:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$185
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/185:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 7/229:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/4![Frontier logo]()
$191
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 June 5, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated June 5, 2026.
This Super.com deal was found by Cheapflights users on 5/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 5/31![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 6/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Deal found 6/1![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 5/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 5/31![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Deal found 6/3![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/247:43 am
DEN
- RFD
1 stop23h 46m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/35:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/4![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/246:30 am
DEN
- MDW
1 stop14h 41m
Frontier
Deal found 6/4![Frontier logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 5/31. 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.
Sat 6/135:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 5/31![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/86:30 am
DEN
- ORD
1 stop12h 25m
Frontier
Deal found 6/4![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/66:30 am
DEN
- MDW
1 stop14h 33m
Frontier
Deal found 6/3![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/126:30 am
DEN
- ORD
1 stop12h 23m
Frontier
Deal found 6/4![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/87:56 am
DEN
- RFD
1 stop23h 33m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$101
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 June 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $184 (Kiwi.com) |
One-way from | $88 (Super.com) |
Popular in | March |
Cheapest in | August |
Average price | $259 |
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 June 5, 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
Thu 8/13
8:29 pm-11:59 pm
Nonstop2h 30m
Chicago O'Hare Intl
Tue 8/18
1:30 pm-3:17 pm
Nonstop2h 47m
$227
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 7/1
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Sat 7/4
6:59 am-8:49 am
Nonstop2h 50m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 7/18
7:10 pm-10:49 pm
Nonstop2h 39m
Chicago O'Hare Intl
Wed 7/29
9:50 pm-11:48 pm
Nonstop2h 58m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 7/1
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Sun 7/5
6:00 am-7:41 am
Nonstop2h 41m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 10/10
11:10 am-4:49 pm
1 stop4h 39m
Chicago O'Hare Intl
Tue 10/13
6:00 am-12:03 pm
1 stop7h 03m
$247
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 10/7
10:30 am-6:40 pm
1 stop7h 10m
Chicago O'Hare Intl
Sat 10/10
8:55 am-2:03 pm
1 stop6h 08m
$247
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 10/7
4:00 pm-9:34 pm
1 stop4h 34m
Chicago O'Hare Intl
Tue 10/13
6:00 am-12:03 pm
1 stop7h 03m
$247
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 9/12
4:00 pm-9:34 pm
1 stop4h 34m
Chicago O'Hare Intl
Mon 9/14
5:42 pm-11:25 pm
1 stop6h 43m
$257
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 9/12
11:15 am-4:48 pm
1 stop4h 33m
Chicago O'Hare Intl
Sat 9/19
7:01 am-1:51 pm
1 stop7h 50m
$257
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 10/7
12:55 am-8:00 am
1 stop6h 05m
Chicago O'Hare Intl
Tue 10/13
7:40 pm-10:59 pm
1 stop4h 19m
$257
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 June 5, 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 55% 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 June 5, 2026.
The most flights from BK9 to CHI are scheduled on a Thursday (83 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 May 30, 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 at noon 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 June 5, 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 June 5, 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 June 5, 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 June 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$318 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$167 | Average$382 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$175 | Average$419 | FlexibilityNo cancel fee | On-time69% |