$83+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Mar 29 — Apr 51
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 September, booked 79 days in advance, depart on a Thursday or Friday 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 February 27, 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 February 27, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Fri 4/32:29 pm
ORD
- DEN
Nonstop3h 20m
Frontier
Deal found 2/22![Frontier logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mon 3/237:39 pm
ORD
- DEN
1 stop15h 05m
Frontier
Deal found 2/24![Frontier logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Mon 3/237:39 pm
ORD
- DEN
1 stop15h 05m
Frontier
Deal found 2/24![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:15 pm
DEN
- ORD
1 stop6h 37m
Frontier
Sun 4/192:00 pm
ORD
- DEN
1 stop7h 20m
Frontier
Deal found 2/25![Frontier logo]()
$144
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/296:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Mon 3/306:20 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 2/25![Frontier logo]()
$145
This Frontier deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Sun 5/1710:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 2/25![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:07 pm
DEN
- MDW
1 stop8h 12m
Frontier
Thu 4/303:27 pm
MDW
- DEN
1 stop9h 53m
Frontier
Deal found 2/24![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2111:59 pm
DEN
- ORD
1 stop9h 03m
Multiple Airlines
Fri 4/243:15 pm
ORD
- DEN
1 stop8h 19m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:09 pm
DEN
- MDW
1 stop8h 10m
Frontier
Sat 5/26:00 am
MDW
- DEN
1 stop7h 14m
Frontier
Deal found 2/25![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:30 am
DEN
- ORD
1 stop7h 49m
Multiple Airlines
Mon 5/114:28 pm
ORD
- DEN
1 stop7h 35m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Thu 4/95:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 2/25![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:45 pm
DEN
- ORD
1 stop6h 31m
Frontier
Tue 5/125:01 am
ORD
- DEN
1 stop8h 08m
Frontier
Deal found 2/25![Frontier logo]()
$149
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 February 27, 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 February 27, 2026.
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:23 pm
DEN
- ORD
Nonstop2h 29m
United Airlines
Tue 3/312:35 pm
ORD
- DEN
Nonstop2h 54m
United Airlines
Deal found 2/23![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/96:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 5/119:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/23![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/16:10 am
DEN
- MDW
1 stop5h 19m
Delta
Sat 4/49:30 am
MDW
- DEN
1 stop5h 38m
Delta
Deal found 2/23![Delta logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:09 pm
DEN
- RFD
2 stops19h 38m
Multiple Airlines
Fri 5/18:35 pm
RFD
- DEN
1 stop14h 08m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/266:20 am
DEN
- MDW
Nonstop2h 25m
Southwest
Mon 3/309:40 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/23![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:35 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Mon 4/275:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/24![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:15 am
DEN
- ORD
1 stop6h 00m
Southwest
Mon 4/276:15 pm
ORD
- DEN
Nonstop2h 50m
Southwest
Deal found 2/25![Southwest logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:09 pm
DEN
- RFD
2 stops21h 10m
Multiple Airlines
Fri 5/18:35 pm
RFD
- DEN
1 stop17h 20m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:35 am
DEN
- ORD
1 stop7h 35m
Delta
Mon 4/69:50 am
ORD
- DEN
1 stop8h 27m
Delta
Deal found 2/26![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/276:00 am
DEN
- ORD
Nonstop2h 38m
United Airlines
Sun 3/299:49 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 2/22![United Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:05 am
DEN
- MDW
1 stop5h 37m
Delta
Sat 5/309:23 am
MDW
- DEN
1 stop7h 13m
Delta
Deal found 2/25![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 3/315:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/25![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:15 am
DEN
- ORD
1 stop6h 00m
Southwest
Thu 4/303:45 pm
ORD
- DEN
2 stops9h 00m
Southwest
Deal found 2/25![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/28:52 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Sat 4/44:10 pm
ORD
- DEN
Nonstop2h 56m
United Airlines
Deal found 2/23![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:35 am
DEN
- MDW
1 stop7h 18m
Delta
Sun 4/129:35 am
MDW
- DEN
1 stop5h 31m
Delta
Deal found 2/26![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 4/134:05 pm
MDW
- DEN
1 stop4h 15m
Southwest
Deal found 2/25![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 7/292:47 pm
DEN
- RFD
1 stop16h 42m
Multiple Airlines
Mon 8/39:13 pm
RFD
- DEN
1 stop13h 04m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$338
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:40 am
DEN
- MDW
2 stops5h 15m
Southwest
Thu 4/305:30 am
MDW
- DEN
1 stop5h 45m
Southwest
Deal found 2/25![Southwest logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:00 am
DEN
- RFD
1 stop10h 00m
Multiple Airlines
Mon 6/159:10 pm
RFD
- DEN
1 stop13h 07m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$378
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/35:30 am
DEN
- ORD
1 stop7h 25m
Southwest
Mon 4/66:25 pm
ORD
- DEN
Nonstop2h 50m
Southwest
Deal found 2/22![Southwest logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:00 am
DEN
- RFD
1 stop10h 00m
Multiple Airlines
Sun 6/149:19 am
RFD
- DEN
1 stop13h 11m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:20 am
DEN
- MDW
Nonstop2h 25m
Southwest
Mon 3/309:40 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/26![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/143:05 pm
DEN
- ORD
1 stop6h 50m
Southwest
Sun 4/194:15 pm
ORD
- DEN
2 stops9h 05m
Southwest
Deal found 2/24![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/224:20 pm
DEN
- RFD
1 stop18h 51m
Multiple Airlines
Sun 5/241:11 pm
RFD
- DEN
1 stop12h 02m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/35:30 am
DEN
- ORD
1 stop7h 25m
Southwest
Fri 4/34:55 pm
ORD
- DEN
1 stop7h 40m
Southwest
Deal found 2/23![Southwest logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 6/202:47 pm
DEN
- RFD
1 stop16h 42m
Multiple Airlines
Sun 6/289:19 am
RFD
- DEN
1 stop13h 11m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 6/242:47 pm
DEN
- RFD
1 stop16h 42m
Multiple Airlines
Sun 6/281:13 pm
RFD
- DEN
1 stop9h 16m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 5/232:45 pm
DEN
- ORD
1 stop6h 35m
Southwest
Mon 5/253:45 pm
ORD
- DEN
1 stop6h 05m
Southwest
Deal found 2/22![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:05 am
DEN
- ORD
2 stops8h 25m
Southwest
Sun 4/194:15 pm
ORD
- DEN
2 stops9h 05m
Southwest
Deal found 2/25![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:00 am
DEN
- RFD
1 stop11h 15m
Multiple Airlines
Sun 6/289:19 am
RFD
- DEN
1 stop13h 11m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$510
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated February 27, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated February 27, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Mon 3/237:39 pm
ORD
- DEN
1 stop15h 05m
Frontier
Deal found 2/24![Frontier logo]()
$143
This Super.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Sat 3/216:00 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 2/26![Frontier logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mon 3/237:39 pm
ORD
- DEN
1 stop15h 05m
Frontier
Deal found 2/24![Frontier logo]()
$142
This Super.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mon 3/308:55 pm
ORD
- DEN
1 stop8h 01m
Frontier
Deal found 2/24![Frontier logo]()
$144
This Cheapflightsfares deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Mon 3/306:20 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 2/24![Frontier logo]()
$149
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Fri 4/32:29 pm
ORD
- DEN
Nonstop3h 20m
Frontier
Deal found 2/22![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 4/47:15 am
ORD
- DEN
1 stop9h 51m
Frontier
Deal found 2/24![Frontier logo]()
$152
This Super.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mon 3/308:55 pm
ORD
- DEN
1 stop8h 01m
Frontier
Deal found 2/24![Frontier logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/296:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Mon 3/306:20 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 2/25![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/318:17 am
DEN
- ORD
1 stop6h 18m
Frontier
Sun 4/58:30 am
ORD
- DEN
1 stop23h 05m
Frontier
Deal found 2/23![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Thu 4/95:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 2/25![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Tue 4/72:56 pm
MDW
- DEN
1 stop9h 08m
Frontier
Deal found 2/25![Frontier logo]()
$160
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 February 27, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated February 27, 2026.
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:44 pm
DEN
- ORD
Nonstop2h 36m
United Airlines
Deal found 2/24![United Airlines logo]()
$83
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 2/24![Southwest logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/202:30 pm
DEN
- ORD
1 stop14h 20m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 2/24![Southwest logo]()
$84
This Super.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/1811:59 pm
DEN
- ORD
1 stop9h 53m
Frontier
Deal found 2/23![Frontier logo]()
$85
This Expedia deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:09 pm
DEN
- MDW
1 stop8h 10m
Frontier
Deal found 2/25![Frontier logo]()
$85
This Frontier deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1211:59 pm
DEN
- ORD
1 stop9h 55m
Frontier
Deal found 2/25![Frontier logo]()
$86
This Priceline deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Deal found 2/25![Frontier logo]()
$86
This Super.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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.
Mon 3/309:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 2/23![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/110:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 2/24![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
DEN
- MDW
1 stop15h 21m
Frontier
Deal found 2/24![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/68:00 am
DEN
- ORD
1 stop27h 39m
Frontier
Deal found 2/25![Frontier logo]()
$89
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 February 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $139 (Cheapflightsfares) |
One-way from | $83 (United Airlines) |
Popular in | November |
Cheapest in | August |
Average price | $237 |
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 February 27, 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
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 3/24
8:23 pm-11:52 pm
Nonstop2h 29m
Chicago O'Hare Intl
Tue 3/31
2:35 pm-4:29 pm
Nonstop2h 54m
$179
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 5/9
6:30 am-9:50 am
Nonstop2h 20m
Chicago Midway
Mon 5/11
9:35 pm-11:15 pm
Nonstop2h 40m
$179
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 3/26
6:20 am-9:45 am
Nonstop2h 25m
Chicago Midway
Mon 3/30
9:40 pm-11:20 pm
Nonstop2h 40m
$181
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 4/24
5:35 pm-9:05 pm
Nonstop2h 30m
Chicago Midway
Mon 4/27
5:15 pm-6:55 pm
Nonstop2h 40m
$181
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 4/22
6:15 am-1:15 pm
1 stop6h 00m
Chicago O'Hare Intl
Mon 4/27
6:15 pm-8:05 pm
Nonstop2h 50m
$190
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 4/1
6:10 am-12:29 pm
1 stop5h 19m
Chicago Midway
Sat 4/4
9:30 am-2:08 pm
1 stop5h 38m
$200
DenverChicago
DEN - RFD
DENRFD
Denver Intl
Wed 4/29
1:09 pm-9:47 am
2 stops19h 38m
Chicago Greater Rockford
Fri 5/1
8:35 pm-9:43 am
1 stop14h 08m
$202
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 3/28
5:55 am-9:20 am
Nonstop2h 25m
Chicago Midway
Tue 3/31
5:35 pm-7:15 pm
Nonstop2h 40m
$211
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 4/29
6:15 am-1:15 pm
1 stop6h 00m
Chicago O'Hare Intl
Thu 4/30
3:45 pm-11:45 pm
2 stops9h 00m
$217
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 4/10
8:20 pm-11:40 pm
Nonstop2h 20m
Chicago Midway
Mon 4/13
4:05 pm-7:20 pm
1 stop4h 15m
$217
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-MDW
DEN-ORD
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-MDW
DEN-ORD
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 February 20, 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 $126). 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 February 27, 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 February 21, 2026.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Saturday evenings 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 February 27, 2026.
The most flights from BK9 to CHI are scheduled on a Thursday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 February 27, 2026.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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
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 February 27, 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 February 27, 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 February 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$289 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$394 | FlexibilityNo cancel fee | On-time69% |