$102+ Cheap flights from Breckenridge, CO to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 1 — Aug 81
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 August, 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 July 2, 2026.
Explore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
This Trip.com deal was found by Cheapflights users on 6/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:17 pm
DEN
- ORD
1 stop6h 07m
Frontier
Mon 9/2810:40 pm
ORD
- DEN
Nonstop2h 49m
Frontier
Deal found 6/28![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 6/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:25 am
DEN
- ORD
Nonstop2h 36m
Frontier
Tue 10/1311:06 am
ORD
- DEN
Nonstop2h 54m
Frontier
Deal found 6/28![Frontier logo]()
$179
This Super.com deal was found by Cheapflights users on 6/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/49:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/30![Frontier logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Mon 8/242:41 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 6/28![Frontier logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Fri 8/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Sat 8/159:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/30![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 6/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Mon 8/109:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/29![Frontier logo]()
$183
This Super.com deal was found by Cheapflights users on 6/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/289:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/30![Frontier logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:55 am
DEN
- ORD
Nonstop2h 41m
Frontier
Tue 9/87:44 pm
ORD
- DEN
1 stop14h 43m
Frontier
Deal found 7/2![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Tue 8/45:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 8/129:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/29![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 8/259:20 am
ORD
- DEN
1 stop11h 57m
Frontier
Deal found 6/28![Frontier logo]()
$189
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sat 8/227:15 am
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 8/256:00 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 7/2![Southwest logo]()
$205
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Wed 8/2611:50 am
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 6/28![Frontier logo]()
$210
Best flights from Breckenridge to ChicagoDiscover carefully curated flight deals from Breckenridge to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from Breckenridge to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 8/257:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 9/99:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/1![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 6/28. 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.
Thu 8/276:05 am
DEN
- ORD
1 stop6h 03m
Delta
Tue 9/16:00 am
ORD
- DEN
1 stop4h 59m
Delta
Deal found 6/28![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/27. 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 7/244:29 pm
DEN
- ORD
Nonstop2h 45m
United Airlines
Mon 7/275:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 6/27![United Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Mon 8/179:15 am
DEN
- RFD
1 stop10h 19m
Multiple Airlines
Sun 8/239:35 pm
RFD
- DEN
1 stop7h 13m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 7/1. 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 8/278:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 9/112:00 pm
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 7/1![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:59 am
DEN
- MDW
1 stop7h 18m
Delta
Mon 8/177:25 pm
MDW
- DEN
1 stop5h 09m
Delta
Deal found 6/29![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 6/27. 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 9/1511:15 am
DEN
- MDW
1 stop3h 45m
Southwest
Wed 9/161:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 6/27![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 6/27. 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.
Thu 8/202:22 pm
DEN
- ORD
1 stop5h 08m
Delta
Tue 8/256:45 pm
ORD
- DEN
1 stop5h 49m
Delta
Deal found 6/27![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:15 pm
DEN
- MDW
1 stop3h 30m
Southwest
Sat 8/156:50 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 6/30![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 7/2811:08 am
DEN
- ORD
1 stop4h 51m
Delta
Thu 8/65:20 pm
ORD
- DEN
1 stop6h 28m
Delta
Deal found 7/1![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/175:00 pm
MDW
- DEN
1 stop3h 50m
Southwest
Deal found 6/30![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 6/27. 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.
Thu 8/1310:19 am
DEN
- ORD
1 stop7h 10m
Delta
Sat 8/156:00 am
ORD
- DEN
1 stop7h 08m
Delta
Deal found 6/27![Delta logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Wed 7/297:56 am
DEN
- RFD
1 stop23h 33m
Multiple Airlines
Sun 8/29:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 7/1. 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 9/53:05 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 9/139:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 6/29![Multiple Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 7/1. 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.
Thu 9/310:19 am
DEN
- ORD
1 stop7h 10m
Delta
Sat 9/56:59 am
ORD
- DEN
1 stop7h 18m
Delta
Deal found 7/1![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 7/1. 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.
Fri 8/288:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 9/29:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 7/1![Southwest logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Thu 8/610:36 pm
DEN
- RFD
1 stop20h 58m
Multiple Airlines
Sun 8/99:21 am
RFD
- DEN
1 stop6h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 6/28. 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 9/1211:10 am
DEN
- ORD
1 stop5h 23m
Delta
Sun 9/135:10 pm
ORD
- DEN
1 stop5h 23m
Delta
Deal found 6/28![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 7/1. 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 9/106:30 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Sun 9/138:45 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 9/1010:45 pm
DEN
- RFD
1 stop18h 26m
Multiple Airlines
Sun 9/133:53 pm
RFD
- DEN
1 stop6h 56m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:05 am
DEN
- ORD
1 stop5h 54m
Delta
Sun 9/135:50 pm
ORD
- DEN
1 stop6h 45m
Delta
Deal found 6/29![Delta logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 9/248:30 am
DEN
- RFD
1 stop11h 09m
Multiple Airlines
Sun 9/273:53 pm
RFD
- DEN
1 stop22h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:55 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 8/307:55 am
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 6/30![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:59 am
DEN
- ORD
1 stop6h 00m
Delta
Sat 7/253:55 pm
ORD
- DEN
1 stop4h 32m
Delta
Deal found 6/29![Delta logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 8/208:31 am
DEN
- RFD
1 stop5h 38m
Multiple Airlines
Sun 8/239:35 pm
RFD
- DEN
1 stop7h 13m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 6/27. 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.
Thu 7/1612:59 am
DEN
- ORD
1 stop6h 00m
Delta
Wed 7/228:27 am
ORD
- DEN
1 stop4h 38m
Delta
Deal found 6/27![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 am
DEN
- ORD
1 stop6h 45m
Delta
Mon 8/105:57 pm
ORD
- DEN
1 stop6h 37m
Delta
Deal found 6/30![Delta logo]()
$382
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated July 2, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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.
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/219:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 7/1![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 6/27. 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.
Sat 7/115:05 am
DEN
- ORD
1 stop10h 03m
Frontier
Wed 7/159:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/27![Frontier logo]()
$202
This Super.com deal was found by Cheapflights users on 6/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/219:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/29![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sun 7/125:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/219:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/28![Frontier logo]()
$214
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:15 am
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 7/2912:20 pm
MDW
- DEN
1 stop5h 20m
Southwest
Deal found 6/30![Southwest logo]()
$215
This Expedia deal was found by Cheapflights users on 6/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:58 am
DEN
- MDW
1 stop11h 05m
Frontier
Wed 8/56:05 am
MDW
- DEN
1 stop8h 56m
Frontier
Deal found 6/29![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 8/189:00 am
MDW
- DEN
1 stop4h 55m
Southwest
Deal found 6/30![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 7/1. 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 8/1511:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Sat 8/222:15 pm
MDW
- DEN
1 stop5h 15m
Southwest
Deal found 7/1![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 6/29. 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 8/1511:10 am
DEN
- MDW
1 stop5h 00m
Southwest
Wed 8/191:55 pm
MDW
- DEN
2 stops6h 55m
Southwest
Deal found 6/29![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 7/1. 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 8/156:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/175:00 pm
MDW
- DEN
1 stop3h 50m
Southwest
Deal found 7/1![Southwest logo]()
$222
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:59 pm
DEN
- MDW
1 stop9h 56m
Frontier
Wed 8/2611:50 am
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 6/28![Frontier logo]()
$210
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:20 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 8/2510:05 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/30![Southwest logo]()
$205
One-way flights from Breckenridge to ChicagoSearch for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Super.com deal was found by Cheapflights users on 6/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:00 am
DEN
- ORD
1 stop8h 53m
Frontier
Deal found 6/29![Frontier logo]()
$102
This iWofly deal was found by Cheapflights users on 6/30. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 6/30![Frontier logo]()
$102
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 7/219:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/30![United Airlines logo]()
$103
This Southwest deal was found by Cheapflights users on 7/1. 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 7/255:15 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 7/1![Southwest logo]()
$103
This United Airlines deal was found by Cheapflights users on 6/29. 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 8/67:40 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/29![United Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 6/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 6/30![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 6/30. 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 8/267:00 am
DEN
- ORD
1 stop7h 59m
Frontier
Deal found 6/30![Frontier logo]()
$105
This Expedia deal was found by Cheapflights users on 6/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 6/28![Frontier logo]()
$105
This Booking.com deal was found by Cheapflights users on 6/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:58 am
DEN
- ORD
1 stop8h 55m
Frontier
Deal found 6/28![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:40 am
DEN
- MDW
1 stop3h 45m
Southwest
Deal found 6/30![Southwest logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 Cheapflightsfares 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
Deal found 6/28![Frontier logo]()
$109
This Expedia deal was found by Cheapflights users on 6/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/28![Frontier logo]()
$111
Find flight deals from Breckenridge to Chicago
Keep the following information in mind while searching for Breckenridge to Chicago flight deals. Data was last updated July 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 (Trip.com) |
One-way from | $102 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $258 |
Cheapflights Fare Finder
Customize your flight search to find flights from Breckenridge to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 2, 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 8/25
7:25 pm-10:50 pm
Nonstop2h 25m
Chicago Midway
Wed 9/9
9:00 am-12:55 pm
1 stop4h 55m
$211
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 8/27
8:25 pm-11:45 pm
Nonstop2h 20m
Chicago Midway
Tue 9/1
12:00 pm-1:30 pm
Nonstop2h 30m
$216
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 9/15
11:15 am-4:00 pm
1 stop3h 45m
Chicago Midway
Wed 9/16
1:55 pm-7:50 pm
2 stops6h 55m
$221
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 8/13
3:15 pm-7:45 pm
1 stop3h 30m
Chicago Midway
Sat 8/15
6:50 am-8:20 am
Nonstop2h 30m
$222
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 8/15
6:00 am-9:20 am
Nonstop2h 20m
Chicago Midway
Mon 8/17
5:00 pm-7:50 pm
1 stop3h 50m
$222
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 8/27
6:05 am-1:08 pm
1 stop6h 03m
Chicago O'Hare Intl
Tue 9/1
6:00 am-9:59 am
1 stop4h 59m
$226
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 8/14
12:59 am-9:17 am
1 stop7h 18m
Chicago Midway
Mon 8/17
7:25 pm-11:34 pm
1 stop5h 09m
$226
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 9/5
3:05 pm-6:25 pm
Nonstop2h 20m
Chicago Midway
Sun 9/13
9:30 am-11:05 am
Nonstop2h 35m
$235
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 8/20
2:22 pm-8:30 pm
1 stop5h 08m
Chicago O'Hare Intl
Tue 8/25
6:45 pm-11:34 pm
1 stop5h 49m
$236
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 7/28
11:08 am-4:59 pm
1 stop4h 51m
Chicago O'Hare Intl
Thu 8/6
5:20 pm-10:48 pm
1 stop6h 28m
$236
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Breckenridge to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Breckenridge with our price prediction graph.
DEN-ORD
DEN-MDW
DEN-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Breckenridge to Chicago
BK9-CHI
DEN-ORD
DEN-MDW
DEN-RFD
What is the cheapest time of day to fly from BK9 to CHI?
Find hourly flight availability from Breckenridge to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 2, 2026.
When flying from Breckenridge to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 54% versus a flight at noon.
Weekly flight availability from Breckenridge to Chicago
Explore weekly flight availability from Breckenridge to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 2, 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 (18 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 June 27, 2026.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 2, 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.
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Alternative routes for Breckenridge to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 2, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Breckenridge to Chicago by cabin class
Find flights from Breckenridge to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Breckenridge and Chicago flights
Browse other Breckenridge and Chicago flight options. Last updated on July 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Breckenridge to Chicago
Discover the top 5 airlines that operate flights from Breckenridge to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$76 | Average$188 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$332 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$167 | Average$394 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$423 | FlexibilityNo cancel fee | On-time69% |