$103+ Cheap flights from Breckenridge, CO to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Sep 27 — Oct 41
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 December, booked 79 days in advance, depart on a Friday or Thursday and return on a Wednesday
Cheap flight deals from Breckenridge to Chicago
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Cheapest flights from Breckenridge to ChicagoExplore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
Explore the most affordable flight options available from Breckenridge to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 9/177:12 pm -
1 stop26h 47m
Sat 9/196:30 am -
Nonstop2h 45m
Deal found 8/24![Frontier logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 8/27. 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 9/198:55 pm -
Nonstop2h 28m
Sun 9/278:55 pm -
1 stop14h 12m
Deal found 8/27![Frontier logo]()
$163
This Frontier deal was found by Cheapflights users on 8/24. 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.
Thu 9/248:55 pm -
Nonstop2h 28m
Wed 9/307:28 pm -
1 stop13h 36m
Deal found 8/24![Frontier logo]()
$164
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:55 pm -
Nonstop2h 28m
Sun 9/206:00 am -
1 stop6h 59m
Deal found 8/27![Frontier logo]()
$165
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:55 pm -
Nonstop2h 28m
Tue 9/226:30 am -
Nonstop2h 45m
Deal found 8/27![Frontier logo]()
$166
This Super.com deal was found by Cheapflights users on 8/23. 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.
Thu 9/108:55 pm -
Nonstop2h 28m
Tue 9/156:30 am -
Nonstop2h 45m
Deal found 8/23![Frontier logo]()
$167
This Frontier deal was found by Cheapflights users on 8/24. 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.
Tue 9/158:55 pm -
Nonstop2h 28m
Sun 9/206:30 am -
Nonstop2h 45m
Deal found 8/24![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:45 am -
Nonstop2h 36m
Tue 9/221:21 pm -
1 stop11h 23m
Deal found 8/27![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:55 pm -
Nonstop2h 28m
Mon 9/216:00 am -
1 stop11h 01m
Deal found 8/27![Frontier logo]()
$170
This Super.com deal was found by Cheapflights users on 8/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:55 pm -
Nonstop2h 28m
Mon 9/146:30 am -
Nonstop2h 45m
Deal found 8/27![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 8/27. 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.
Wed 9/236:38 pm -
1 stop10h 00m
Sat 9/267:25 am -
1 stop25h 40m
Deal found 8/27![Frontier logo]()
$172
This Super.com deal was found by Cheapflights users on 8/26. 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 10/88:55 pm -
Nonstop2h 29m
Wed 10/146:30 am -
Nonstop2h 49m
Deal found 8/26![Frontier logo]()
$173
Best flights from Breckenridge to ChicagoDiscover carefully curated flight deals from Breckenridge to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
Discover carefully curated flight deals from Breckenridge to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/23. 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 10/155:50 am -
Nonstop2h 20m
Mon 10/196:25 pm -
1 stop5h 15m
Deal found 8/23![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:10 pm -
Nonstop2h 35m
Mon 9/215:55 am -
Nonstop2h 39m
Deal found 8/27![United Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 8/25. 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.
Sat 9/196:30 am -
1 stop5h 09m
Tue 9/222:00 pm -
1 stop7h 05m
Deal found 8/25![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:37 pm -
1 stop10h 56m
Sun 11/158:37 pm -
1 stop14h 11m
Deal found 8/27![Multiple Airlines logo]()
$283
This KAYAK deal was found by Cheapflights users on 8/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:13 pm -
1 stop5h 51m
Thu 9/1710:30 pm -
Nonstop2h 47m
Deal found 8/24![American Airlines logo]()
$315
This Sun Country Air deal was found by Cheapflights users on 8/23. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:20 am -
1 stop23h 00m
Mon 11/309:24 am -
1 stop10h 05m
Deal found 8/23![Sun Country Air logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 8/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:20 am -
2 stops14h 39m
Sat 11/72:15 pm -
1 stop9h 35m
Deal found 8/27![Alaska Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 8/23. 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 10/2911:20 am -
1 stop4h 55m
Mon 11/210:05 am -
1 stop4h 20m
Deal found 8/23![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 8/23. 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.
Wed 10/711:00 am -
1 stop4h 05m
Wed 10/149:25 am -
1 stop5h 45m
Deal found 8/23![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:48 pm -
Nonstop2h 42m
Sun 9/205:55 am -
Nonstop2h 39m
Deal found 8/25![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 8/25. 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 10/2810:45 am -
2 stops5h 05m
Mon 11/210:05 am -
1 stop4h 20m
Deal found 8/25![Southwest logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 10/2210:44 pm -
1 stop11h 43m
Sun 10/258:53 pm -
1 stop19h 11m
Deal found 8/24![Multiple Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 8/24. 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 10/1611:20 am -
1 stop4h 55m
Tue 10/201:05 pm -
1 stop4h 25m
Deal found 8/24![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 am -
Nonstop2h 42m
Sun 9/205:00 am -
Nonstop2h 39m
Deal found 8/25![United Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:10 pm -
1 stop4h 50m
Mon 11/912:45 pm -
1 stop4h 50m
Deal found 8/27![Southwest logo]()
$240
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Sat 10/36:10 pm -
Nonstop2h 42m
Mon 10/510:00 pm -
Nonstop2h 54m
Deal found 8/23![United Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/910:38 am -
1 stop27h 25m
Sun 9/133:53 pm -
1 stop26h 23m
Deal found 8/25![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:30 am -
1 stop5h 29m
Sun 9/206:10 am -
1 stop4h 53m
Deal found 8/24![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 8/26. 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.
Sat 10/1012:30 pm -
1 stop4h 30m
Sat 10/176:35 am -
1 stop5h 00m
Deal found 8/26![Southwest logo]()
$246
This KAYAK deal was found by Cheapflights users on 8/26. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:09 pm -
Nonstop2h 41m
Wed 10/149:40 am -
1 stop7h 24m
Deal found 8/26![American Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/257:00 am -
1 stop10h 11m
Sun 9/279:29 pm -
1 stop13h 38m
Deal found 8/23![Multiple Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Tue 9/157:10 pm -
Nonstop2h 36m
Thu 9/175:55 am -
Nonstop2h 39m
Deal found 8/27![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 8/24. 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 10/238:55 pm -
Nonstop2h 20m
Sun 10/258:30 am -
Nonstop2h 40m
Deal found 8/24![Southwest logo]()
$256
This KAYAK deal was found by Cheapflights users on 8/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:56 am -
Nonstop2h 44m
Thu 9/106:45 am -
Nonstop2h 52m
Deal found 8/27![American Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Thu 10/17:30 am -
1 stop11h 43m
Mon 10/510:44 am -
2 stops31h 32m
Deal found 8/26![Multiple Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 8/27. 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.
Wed 10/711:00 am -
1 stop4h 05m
Thu 10/86:05 am -
Nonstop2h 40m
Deal found 8/27![Southwest logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Thu 10/810:44 pm -
1 stop11h 43m
Sun 10/119:33 pm -
2 stops21h 16m
Deal found 8/23![Multiple Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 8/24. 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.
Wed 9/94:40 pm -
Nonstop2h 42m
Sun 9/137:00 am -
Nonstop2h 47m
Deal found 8/24![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 8/26. 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.
Thu 11/511:00 am -
1 stop5h 35m
Sun 11/812:45 pm -
1 stop4h 50m
Deal found 8/26![Southwest logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 10/110:47 pm -
1 stop11h 40m
Sun 10/49:36 pm -
1 stop13h 31m
Deal found 8/24![Multiple Airlines logo]()
$372
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated August 28, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:55 am -
Nonstop2h 41m
Sat 9/126:30 am -
Nonstop2h 45m
Deal found 8/23![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:55 am -
Nonstop2h 41m
Mon 9/146:30 am -
Nonstop2h 45m
Deal found 8/27![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 9/59:55 am -
Nonstop2h 41m
Sun 9/62:41 pm -
Nonstop3h 04m
Deal found 8/24![Frontier logo]()
$199
This Cheapflightsfares deal was found by Cheapflights users on 8/28. 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 9/59:55 am -
Nonstop2h 41m
Wed 9/96:30 am -
Nonstop2h 45m
Deal found 8/28![Frontier logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 8/25. 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 9/69:55 am -
Nonstop2h 41m
Thu 9/172:46 pm -
1 stop22h 24m
Deal found 8/25![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 8/27. 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.
Sun 9/69:55 am -
Nonstop2h 41m
Wed 9/96:30 am -
Nonstop2h 45m
Deal found 8/27![Frontier logo]()
$190
This Super.com deal was found by Cheapflights users on 8/24. 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.
Sun 9/69:55 am -
Nonstop2h 41m
Sat 9/126:30 am -
Nonstop2h 45m
Deal found 8/24![Frontier logo]()
$201
This Southwest deal was found by Cheapflights users on 8/24. 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 9/157:25 pm -
Nonstop2h 30m
Sat 9/196:50 am -
Nonstop2h 30m
Deal found 8/24![Southwest logo]()
$213
This Expedia deal was found by Cheapflights users on 8/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:44 am -
1 stop6h 07m
Mon 9/2812:54 pm -
1 stop9h 55m
Deal found 8/24![Frontier logo]()
$174
This FlightHub deal was found by Cheapflights users on 8/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:44 am -
1 stop6h 07m
Sat 9/261:06 pm -
1 stop9h 43m
Deal found 8/25![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 8/25. 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.
Tue 9/2210:44 am -
1 stop6h 02m
Sat 9/261:06 pm -
1 stop9h 43m
Deal found 8/25![Frontier logo]()
$186
This Orbitz deal was found by Cheapflights users on 8/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:44 am -
1 stop6h 02m
Thu 10/112:54 pm -
1 stop9h 55m
Deal found 8/26![Frontier logo]()
$198
One-way flights from Breckenridge to ChicagoSearch for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:16 pm -
1 stop16h 01m
Deal found 8/23![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 8/24. 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.
Mon 10/2610:38 am -
1 stop12h 05m
Deal found 8/24![Frontier logo]()
$104
This Booking.com deal was found by Cheapflights users on 8/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:31 am -
1 stop20h 45m
Deal found 8/26![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 8/25. 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.
Wed 10/2110:38 am -
1 stop12h 05m
Deal found 8/25![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 8/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:38 pm -
1 stop10h 00m
Deal found 8/26![Frontier logo]()
$106
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:29 pm -
Nonstop2h 30m
Deal found 8/25![United Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 11/56:46 pm -
1 stop14h 47m
Deal found 8/24![Multiple Airlines logo]()
$107
This Southwest deal was found by Cheapflights users on 8/26. 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.
Thu 10/225:50 am -
Nonstop2h 20m
Deal found 8/26![Southwest logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:09 am -
1 stop7h 08m
Deal found 8/27![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:55 pm -
Nonstop2h 28m
Deal found 8/25![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 8/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:44 am -
1 stop6h 02m
Deal found 8/27![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 8/24. 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 9/128:55 pm -
Nonstop2h 28m
Deal found 8/24![Frontier logo]()
$112
Find flight deals from Breckenridge to Chicago
Keep the following information in mind while searching for Breckenridge to Chicago flight deals. Data was last updated August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $103 (Cheapflightsfares) |
Popular in | July |
Cheapest in | January |
Average price | $277 |
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 7,457,451 searches. Data last updated August 28, 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 Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 10/15
5:50 am-9:10 am
Nonstop2h 20m
Chicago Midway
Mon 10/19
6:25 pm-10:40 pm
1 stop5h 15m
$223
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 10/29
11:20 am-5:15 pm
1 stop4h 55m
Chicago Midway
Mon 11/2
10:05 am-1:25 pm
1 stop4h 20m
$224
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Fri 9/18
7:10 pm-10:45 pm
Nonstop2h 35m
Chicago O'Hare Intl
Mon 9/21
5:55 am-7:34 am
Nonstop2h 39m
$225
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 10/7
11:00 am-4:05 pm
1 stop4h 05m
Chicago Midway
Wed 10/14
9:25 am-2:10 pm
1 stop5h 45m
$228
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 9/19
6:30 am-12:39 pm
1 stop5h 09m
Chicago Midway
Tue 9/22
2:00 pm-8:05 pm
1 stop7h 05m
$233
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 10/28
10:45 am-4:50 pm
2 stops5h 05m
Chicago Midway
Mon 11/2
10:05 am-1:25 pm
1 stop4h 20m
$234
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 10/16
11:20 am-5:15 pm
1 stop4h 55m
Chicago Midway
Tue 10/20
1:05 pm-4:30 pm
1 stop4h 25m
$236
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 11/6
4:10 pm-10:00 pm
1 stop4h 50m
Chicago Midway
Mon 11/9
12:45 pm-4:35 pm
1 stop4h 50m
$240
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 10/10
12:30 pm-6:00 pm
1 stop4h 30m
Chicago Midway
Sat 10/17
6:35 am-10:35 am
1 stop5h 00m
$246
Quickest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 10/23
8:55 pm-12:15 am
Nonstop2h 20m
Chicago Midway
Sun 10/25
8:30 am-10:10 am
Nonstop2h 40m
$256
Showing 1-10 of 59 resultsSorted by cheapest first
Best time to book a flight from Breckenridge to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Breckenridge with our price prediction graph.
DEN-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 August 28, 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 52% versus a flight at noon.
Weekly flight availability from Breckenridge to Chicago
Explore weekly flight availability from Breckenridge to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 28, 2026.
The most flights from BK9 to CHI are scheduled on a Wednesday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Breckenridge to Chicago?
Airfare is below average for this route at the moment.
Breckenridge to Chicago flights typically cost between $171 and $319 in September.The cheapest round-trip price found within the last 5 days was $162 on Frontier (Sep 17-Sep 19).
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 August 22, 2026.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 28, 2026.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Breckenridge to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Breckenridge to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Breckenridge to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Breckenridge and Chicago flights
Browse other Breckenridge and Chicago flight options. Last updated on August 28, 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 7,457,451 searches. Data last updated August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$79 | Average$196 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$346 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$171 | Average$382 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$182 | Average$432 | FlexibilityNo cancel fee | On-time69% |