$84+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Apr 6 — Apr 131
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 August or September, booked 79 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap flight deals from Breckenridge to Chicago
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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 March 7, 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 March 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 4/13:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Deal found 3/2![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Wed 5/1311:59 pm
DEN
- ORD
1 stop21h 40m
Frontier
Sat 5/164:28 pm
ORD
- DEN
1 stop7h 35m
Frontier
Deal found 3/2![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Mon 3/309:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 4/15:15 pm
ORD
- DEN
1 stop14h 20m
Frontier
Deal found 3/2![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Wed 4/1511:07 am
ORD
- DEN
1 stop12h 22m
Frontier
Deal found 3/3![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:00 am
DEN
- ORD
1 stop6h 12m
Frontier
Wed 4/1511:07 am
ORD
- DEN
1 stop12h 22m
Frontier
Deal found 3/3![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Tue 4/212:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/3![Frontier logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 3/254:51 pm
ORD
- DEN
1 stop7h 13m
Frontier
Deal found 3/4![Frontier logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 3/248:55 pm
ORD
- DEN
1 stop8h 01m
Frontier
Deal found 3/3![Frontier logo]()
$154
This Frontier deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:00 am
DEN
- ORD
1 stop6h 12m
Frontier
Mon 4/132:29 pm
ORD
- DEN
Nonstop3h 11m
Frontier
Deal found 3/3![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Mon 4/135:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 3/3![Frontier logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Fri 4/32:29 pm
ORD
- DEN
Nonstop3h 20m
Frontier
Deal found 3/3![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Mon 4/202:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/5![Frontier logo]()
$156
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 March 7, 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 March 7, 2026.
This United Airlines deal was found by Cheapflights users on 3/6. 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.
Wed 6/34:20 pm
DEN
- ORD
Nonstop2h 45m
United Airlines
Mon 6/85:00 am
ORD
- DEN
Nonstop2h 42m
United Airlines
Deal found 3/6![United Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 3/6. 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 4/116:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 4/136:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/6![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 3/6. 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.
Fri 4/1012:35 am
DEN
- ORD
1 stop7h 35m
Delta
Mon 4/1311:00 am
ORD
- DEN
1 stop7h 21m
Delta
Deal found 3/6![Delta logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 4/3010:35 pm
DEN
- RFD
1 stop20h 10m
Multiple Airlines
Thu 5/710:37 am
RFD
- DEN
2 stops22h 32m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 3/6. 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.
Wed 6/311:45 am
DEN
- MDW
1 stop3h 55m
Southwest
Mon 6/85:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 3/6![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:35 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Sun 4/196:55 am
MDW
- DEN
2 stops6h 35m
Southwest
Deal found 3/3![Southwest logo]()
$208
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:40 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sun 6/710:55 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Deal found 3/4![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 3/6. 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.
Thu 5/78:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 5/106:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/6![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 3/6. 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.
Sat 4/46:00 am
DEN
- ORD
Nonstop2h 37m
United Airlines
Tue 4/72:05 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 3/6![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 4/196:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/3![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 6/410:35 pm
DEN
- RFD
1 stop20h 45m
Multiple Airlines
Sun 6/149:19 am
RFD
- DEN
1 stop13h 11m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 3/6. 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.
Wed 6/36:15 am
DEN
- ORD
1 stop6h 00m
Southwest
Mon 6/88:05 pm
ORD
- DEN
1 stop12h 55m
Southwest
Deal found 3/6![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 3/6. 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.
Wed 5/278:17 am
DEN
- ORD
Nonstop2h 25m
United Airlines
Fri 5/299:39 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Deal found 3/6![United Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:40 am
DEN
- MDW
1 stop4h 35m
Southwest
Sat 4/255:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/4![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:00 pm
DEN
- ORD
1 stop6h 55m
Southwest
Mon 5/46:15 pm
ORD
- DEN
Nonstop2h 50m
Southwest
Deal found 3/4![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:47 pm
DEN
- RFD
1 stop16h 44m
Multiple Airlines
Thu 5/2811:27 am
RFD
- DEN
2 stops33h 28m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Fri 4/243:35 pm
MDW
- DEN
1 stop5h 25m
Southwest
Deal found 3/4![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/6. 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 4/45:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Sat 4/116:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/6![Southwest logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Fri 5/222:21 pm
DEN
- RFD
2 stops18h 00m
Multiple Airlines
Mon 5/259:13 pm
RFD
- DEN
1 stop13h 04m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 3/1. 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 4/26:20 am
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 4/85:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/1![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 3/6. 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 4/45:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 4/712:20 pm
MDW
- DEN
1 stop4h 25m
Southwest
Deal found 3/6![Southwest logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:11 am
DEN
- RFD
2 stops21h 34m
Multiple Airlines
Sun 5/249:21 am
RFD
- DEN
1 stop13h 09m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 3/6. 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.
Thu 5/71:00 pm
DEN
- ORD
2 stops9h 55m
Southwest
Sun 5/107:15 pm
ORD
- DEN
1 stop6h 25m
Southwest
Deal found 3/6![Southwest logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:21 pm
DEN
- RFD
2 stops18h 00m
Multiple Airlines
Sun 5/241:11 pm
RFD
- DEN
1 stop9h 18m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 3/2. 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.
Wed 4/86:15 am
DEN
- ORD
1 stop5h 35m
Southwest
Sat 4/112:05 pm
ORD
- DEN
2 stops9h 15m
Southwest
Deal found 3/2![Southwest logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:05 pm
DEN
- RFD
2 stops13h 42m
Multiple Airlines
Thu 4/212:45 pm
RFD
- DEN
1 stop8h 15m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$507
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:30 am
DEN
- ORD
1 stop6h 25m
Southwest
Thu 4/92:40 pm
ORD
- DEN
2 stops9h 20m
Southwest
Deal found 3/1![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 6/32:47 pm
DEN
- RFD
1 stop16h 42m
Multiple Airlines
Sat 6/610:07 am
RFD
- DEN
1 stop13h 57m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$572
This Southwest deal was found by Cheapflights users on 3/1. 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 4/25:30 am
DEN
- ORD
1 stop7h 25m
Southwest
Wed 4/87:45 am
ORD
- DEN
2 stops8h 20m
Southwest
Deal found 3/1![Southwest logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:53 pm
DEN
- RFD
1 stop15h 01m
Multiple Airlines
Mon 4/68:32 pm
RFD
- DEN
1 stop20h 13m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$583
Last-minute flights from Breckenridge to ChicagoDiscover last-minute flight deals from Breckenridge to Chicago. Data last updated March 7, 2026 and is based on user searches.
Discover last-minute flight deals from Breckenridge to Chicago. Data last updated March 7, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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.
Sun 3/156:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Tue 3/177:31 pm
ORD
- DEN
1 stop29h 59m
Frontier
Deal found 3/2![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 3/254:51 pm
ORD
- DEN
1 stop7h 13m
Frontier
Deal found 3/4![Frontier logo]()
$153
This Super.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:25 pm
DEN
- MDW
1 stop20h 34m
Frontier
Sun 4/124:46 pm
MDW
- DEN
1 stop8h 12m
Frontier
Deal found 3/3![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Tue 4/212:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/3![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:20 pm
DEN
- MDW
1 stop8h 17m
Frontier
Mon 4/135:11 pm
MDW
- DEN
1 stop7h 47m
Frontier
Deal found 3/3![Frontier logo]()
$155
This Frontier deal was found by Cheapflights users on 3/5. 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.
Wed 4/151:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Sat 4/186:00 am
MDW
- DEN
1 stop7h 14m
Frontier
Deal found 3/5![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:09 pm
DEN
- MDW
1 stop8h 10m
Frontier
Thu 4/236:00 am
MDW
- DEN
1 stop7h 09m
Frontier
Deal found 3/2![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Mon 4/202:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/5![Frontier logo]()
$156
This Frontier deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Wed 4/226:15 am
MDW
- DEN
1 stop6h 54m
Frontier
Deal found 3/3![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:09 pm
DEN
- MDW
1 stop8h 05m
Frontier
Thu 4/236:00 am
MDW
- DEN
1 stop7h 09m
Frontier
Deal found 3/5![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Mon 4/208:00 am
DEN
- MDW
1 stop13h 21m
Frontier
Mon 4/272:15 pm
MDW
- DEN
1 stop22h 59m
Frontier
Deal found 3/6![Frontier logo]()
$158
This Booking.com deal was found by Cheapflights users on 3/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:59 pm
DEN
- MDW
1 stop9h 29m
Frontier
Mon 5/42:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/5![Frontier logo]()
$161
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 March 7, 2026.
Search for one-way flight options from Breckenridge to Chicago. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
This Flightnetwork deal was found by Cheapflights users on 3/2. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/2![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Mon 4/2011:59 pm
DEN
- MDW
1 stop21h 15m
Frontier
Deal found 3/2![Frontier logo]()
$84
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:03 pm
DEN
- ORD
1 stop28h 57m
Frontier
Deal found 3/3![Frontier logo]()
$86
This Expedia deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Deal found 3/3![Frontier logo]()
$86
This Super.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/110:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 3/3![Frontier logo]()
$87
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:25 am
DEN
- ORD
Nonstop2h 35m
Southwest
Deal found 3/2![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/2![Southwest logo]()
$89
This Frontier deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
DEN
- ORD
Nonstop2h 43m
Frontier
Deal found 3/2![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 3/2. 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 5/96:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 3/2![Southwest logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 3/3![Frontier logo]()
$94
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:05 am
DEN
- MDW
1 stop4h 30m
Southwest
Deal found 3/3![Southwest logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:17 am
DEN
- ORD
1 stop8h 58m
Frontier
Deal found 3/3![Frontier logo]()
$95
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 March 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $146 (Kiwi.com) |
One-way from | $84 (Flightnetwork) |
Popular in | March |
Cheapest in | August |
Average price | $268 |
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 March 7, 2026.
Use the filters below to find and compare flights from Breckenridge to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 6/3
4:20 pm-8:05 pm
Nonstop2h 45m
Chicago O'Hare Intl
Mon 6/8
5:00 am-6:42 am
Nonstop2h 42m
$198
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 4/11
6:30 am-9:50 am
Nonstop2h 20m
Chicago Midway
Mon 4/13
6:00 am-7:40 am
Nonstop2h 40m
$198
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 6/3
11:45 am-4:40 pm
1 stop3h 55m
Chicago Midway
Mon 6/8
5:15 am-6:50 am
Nonstop2h 35m
$204
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 4/17
5:35 pm-9:05 pm
Nonstop2h 30m
Chicago Midway
Sun 4/19
6:55 am-12:30 pm
2 stops6h 35m
$208
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 5/7
8:20 pm-11:40 pm
Nonstop2h 20m
Chicago Midway
Sun 5/10
6:00 am-7:40 am
Nonstop2h 40m
$209
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 4/11
6:30 am-9:50 am
Nonstop2h 20m
Chicago Midway
Sun 4/19
6:00 am-7:40 am
Nonstop2h 40m
$217
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 4/10
12:35 am-9:10 am
1 stop7h 35m
Chicago O'Hare Intl
Mon 4/13
11:00 am-5:21 pm
1 stop7h 21m
$221
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 6/3
6:15 am-1:15 pm
1 stop6h 00m
Chicago O'Hare Intl
Mon 6/8
8:05 pm-8:00 am
1 stop12h 55m
$223
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 4/18
11:40 am-5:15 pm
1 stop4h 35m
Chicago Midway
Sat 4/25
5:30 pm-7:10 pm
Nonstop2h 40m
$223
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 5/1
4:00 pm-11:55 pm
1 stop6h 55m
Chicago O'Hare Intl
Mon 5/4
6:15 pm-8:05 pm
Nonstop2h 50m
$227
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
How far ahead should I book a flight from Breckenridge to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Breckenridge to Chicago. Price data was last updated on March 6, 2026.
The price you pay for your flight from Breckenridge to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Breckenridge to Chicago?
Currently, April is the cheapest month in which you can book a flight from Breckenridge to Chicago (average of $81). Flying from Breckenridge to Chicago in June is currently the most expensive (average of $135). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from BK9 to CHI?
Find hourly flight availability from Breckenridge to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 7, 2026.
When flying from Breckenridge to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 63% versus a flight at noon.
What is the cheapest day to fly from Breckenridge to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Breckenridge to Chicago. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Breckenridge to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Breckenridge to Chicago?
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 March 7, 2026.
Read through reviews of airlines operating flights from Breckenridge to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Breckenridge to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 March 7, 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 March 7, 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 March 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$290 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$394 | FlexibilityNo cancel fee | On-time69% |