$106+ Cheap flights from Breckenridge, CO to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Oct 11 — Oct 181
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 Friday
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 September 11, 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 September 11, 2026.
This Frontier deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 12/33:48 pm -
Nonstop2h 34m
Mon 12/1412:51 pm -
1 stop9h 08m
Deal found 9/7![Frontier logo]()
$163
This Cheapflightsfares deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 12/45:52 pm -
Nonstop2h 29m
Tue 12/88:43 pm -
Nonstop3h 01m
Deal found 9/8![Frontier logo]()
$164
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/38:55 pm -
Nonstop2h 28m
Tue 10/66:30 am -
Nonstop2h 45m
Deal found 9/7![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/28:55 pm -
Nonstop2h 28m
Tue 10/66:30 am -
Nonstop2h 45m
Deal found 9/8![Frontier logo]()
$169
This deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:55 pm -
Nonstop2h 28m
Wed 9/166:30 am -
Nonstop2h 45m
Deal found 9/9![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/16:09 am -
1 stop14h 30m
Sun 10/46:30 am -
Nonstop2h 45m
Deal found 9/5![Frontier logo]()
$171
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Fri 10/238:55 pm -
Nonstop2h 29m
Fri 10/306:30 am -
Nonstop2h 56m
Deal found 9/8![Frontier logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/108:55 pm -
Nonstop2h 29m
Tue 10/137:40 am -
1 stop29h 32m
Deal found 9/7![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:55 pm -
Nonstop2h 29m
Mon 10/196:30 am -
Nonstop2h 49m
Deal found 9/10![Frontier logo]()
$174
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:12 pm -
1 stop16h 13m
Sun 10/256:30 am -
Nonstop2h 49m
Deal found 9/10![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/18:55 pm -
Nonstop2h 28m
Sat 10/36:30 am -
Nonstop2h 45m
Deal found 9/5![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Fri 10/28:55 pm -
Nonstop2h 28m
Mon 10/53:50 pm -
1 stop17h 02m
Deal found 9/9![Frontier logo]()
$177
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 September 11, 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 September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/296:00 am -
Nonstop2h 43m
Tue 9/297:50 pm -
Nonstop2h 54m
Deal found 9/8![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/228:55 pm -
Nonstop2h 25m
Sat 10/245:05 pm -
Nonstop2h 40m
Deal found 9/10![Southwest logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/2910:37 pm -
1 stop11h 50m
Sun 11/18:53 pm -
1 stop27h 56m
Deal found 9/10![Multiple Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:07 am -
1 stop4h 40m
Sun 11/19:29 am -
1 stop6h 38m
Deal found 9/10![Delta logo]()
$296
This KAYAK deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/126:57 pm -
1 stop9h 03m
Wed 10/1410:45 pm -
Nonstop2h 51m
Deal found 9/6![American Airlines logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Thu 10/2212:31 pm -
2 stops16h 09m
Sun 10/256:00 am -
1 stop9h 08m
Deal found 9/6![Alaska Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/26:55 pm -
Nonstop2h 20m
Sat 10/37:25 pm -
Nonstop2h 40m
Deal found 9/10![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/611:40 am -
1 stop3h 40m
Wed 10/710:15 am -
1 stop4h 50m
Deal found 9/9![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/298:35 am -
1 stop4h 20m
Tue 9/294:15 pm -
1 stop4h 40m
Deal found 9/8![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:07 am -
1 stop4h 33m
Wed 10/2811:19 am -
1 stop7h 13m
Deal found 9/6![Delta logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/510:37 pm -
1 stop10h 56m
Sun 11/88:37 pm -
1 stop14h 11m
Deal found 9/10![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:05 am -
1 stop4h 42m
Mon 11/21:27 pm -
1 stop5h 05m
Deal found 9/5![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/66:45 pm -
Nonstop2h 15m
Mon 11/95:55 am -
Nonstop2h 50m
Deal found 9/9![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/238:29 pm -
Nonstop2h 30m
Mon 10/269:47 pm -
Nonstop2h 44m
Deal found 9/6![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/9![Multiple Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 12/61:26 pm -
1 stop5h 17m
Sun 12/136:20 am -
1 stop4h 48m
Deal found 9/7![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/56:30 pm -
1 stop5h 35m
Sat 11/77:35 am -
2 stops7h 55m
Deal found 9/9![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/36:55 am -
1 stop4h 10m
Mon 10/56:05 am -
Nonstop2h 40m
Deal found 9/6![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 -
2 stops20h 11m
Deal found 9/6![Multiple Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/304:20 pm -
1 stop3h 35m
Mon 11/210:05 am -
1 stop4h 20m
Deal found 9/6![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 -
2 stops16h 19m
Deal found 9/10![Multiple Airlines logo]()
$396
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Fri 10/28:08 am -
2 stops14h 51m
Sat 10/38:10 am -
2 stops15h 27m
Deal found 9/10![Alaska Airlines logo]()
$533
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:30 am -
Nonstop2h 20m
Sun 10/47:45 am -
1 stop4h 05m
Deal found 9/7![Southwest logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/3010:50 pm -
1 stop20h 23m
Sun 10/49:36 pm -
1 stop13h 31m
Deal found 9/7![Multiple Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/266:15 am -
1 stop4h 24m
Wed 9/3011:17 am -
1 stop7h 04m
Deal found 9/10![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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
Sun 10/116:00 am -
Nonstop2h 40m
Deal found 9/7![Southwest logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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
Sat 10/38:58 pm -
1 stop13h 45m
Deal found 9/8![Multiple Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/238:45 am -
1 stop7h 14m
Tue 9/295:50 pm -
1 stop6h 45m
Deal found 9/7![Delta logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2010:44 pm -
1 stop13h 33m
Thu 10/298:20 pm -
2 stops24h 55m
Deal found 9/6![Multiple Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/156:30 am -
1 stop5h 29m
Tue 9/228:55 am -
1 stop6h 02m
Deal found 9/9![Delta logo]()
$517
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated September 11, 2026 and is based on user searches.
This deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:55 pm -
Nonstop2h 28m
Wed 9/166:30 am -
Nonstop2h 45m
Deal found 9/9![Frontier logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Mon 9/286:09 am -
1 stop14h 30m
Sun 10/46:30 am -
Nonstop2h 45m
Deal found 9/8![Frontier logo]()
$163
This Cheapflightsfares deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Mon 9/287:30 am -
1 stop21h 08m
Wed 9/306:30 am -
Nonstop2h 45m
Deal found 9/9![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/16:09 am -
1 stop14h 30m
Sun 10/46:30 am -
Nonstop2h 45m
Deal found 9/6![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/18:55 pm -
Nonstop2h 28m
Sat 10/36:30 am -
Nonstop2h 45m
Deal found 9/7![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/28:55 pm -
Nonstop2h 28m
Tue 10/66:30 am -
Nonstop2h 45m
Deal found 9/8![Frontier logo]()
$169
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Fri 10/28:55 pm -
Nonstop2h 28m
Mon 10/53:50 pm -
1 stop17h 02m
Deal found 9/9![Frontier logo]()
$177
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/38:55 pm -
Nonstop2h 28m
Tue 10/66:30 am -
Nonstop2h 45m
Deal found 9/7![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/56:38 pm -
1 stop10h 00m
Tue 10/136:30 am -
Nonstop2h 49m
Deal found 9/10![Frontier logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/108:55 pm -
Nonstop2h 29m
Tue 10/137:40 am -
1 stop29h 32m
Deal found 9/7![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:55 pm -
Nonstop2h 29m
Mon 10/196:30 am -
Nonstop2h 49m
Deal found 9/10![Frontier logo]()
$174
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Fri 10/238:55 pm -
Nonstop2h 29m
Fri 10/306:30 am -
Nonstop2h 56m
Deal found 9/8![Frontier logo]()
$172
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 September 11, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/249:26 pm -
Nonstop2h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:45 pm -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/510:37 pm -
1 stop10h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/236:09 am -
1 stop7h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:41 am -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:55 pm -
Nonstop2h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/259:26 pm -
Nonstop2h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 12/511:55 pm -
1 stop18h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$112
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/63:48 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/49:10 pm -
1 stop19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 12/911:55 pm -
1 stop18h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Mon 9/286:30 am -
1 stop12h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$115
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $163 (Frontier) |
One-way from | $106 (Cheapflightsfares) |
Popular in | July |
Cheapest in | January |
Average price | $271 |
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 September 11, 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 - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Thu 10/1
6:10 pm-9:52 pm
Nonstop2h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$115
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 11/17
7:05 am-10:30 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$115
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 10/22
8:55 pm-12:20 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$115
Quickest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 10/3
5:35 pm-8:55 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$115
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 9/30
12:59 am-9:07 am
1 stop7h 08m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 12/9
6:15 am-1:01 pm
1 stop5h 46m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Fri 11/27
5:58 pm-9:30 pm
Nonstop2h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 12/5
6:00 am-2:30 pm
2 stops7h 30m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Fri 10/9
5:26 pm-3:03 pm
1 stop20h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 10/14
5:40 pm-9:00 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Breckenridge to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Breckenridge with our price prediction graph.
DEN-ORD
DEN-MDW
DEN-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Breckenridge to Chicago
BK9-CHI
DEN-ORD
DEN-MDW
DEN-RFD
What is the cheapest time of day to fly from BK9 to CHI?
Find hourly flight availability from Breckenridge to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 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 51% 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 September 11, 2026.
The most flights from BK9 to CHI are scheduled on a Thursday (81 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (50 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 $213 and $343 in December.The cheapest round-trip price found within the last 5 days was $163 on Frontier (Dec 3-Dec 14).
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 September 5, 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 September 11, 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.
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 September 11, 2026.
Complete your trip
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Breckenridge and Chicago flights
Browse other Breckenridge and Chicago flight options. Last updated on September 11, 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 September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$347 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$171 | Average$383 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$433 | FlexibilityNo cancel fee | On-time69% |