$40+ Cheap flights from Chicago (CHI) to Boca Raton, FL
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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Mar 12 — Mar 191
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Boca Raton 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 Chicago to Boca Raton are usually found in September or January, booked 41 days in advance, depart on a Monday or Sunday and return on a Thursday
Cheap flight deals from Chicago to Boca Raton
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Boca RatonExplore the most affordable flight options available from Chicago to Boca Raton. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 10, 2026.
Explore the most affordable flight options available from Chicago to Boca Raton. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 10, 2026.
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:48 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Tue 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Wed 4/293:47 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$83
This Frontier deal was found by Cheapflights users on 2/10. 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.
Sat 2/2811:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Sat 3/77:15 am
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/10![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 2/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Fri 3/611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/9![Frontier logo]()
$84
This CheapOair deal was found by Cheapflights users on 2/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:05 pm
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Fri 3/136:00 am
MIA
- ORD
Nonstop3h 25m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sun 3/89:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Wed 3/117:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$86
This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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 2/237:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Fri 2/277:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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.
Fri 5/87:15 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Mon 5/113:27 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/9![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 2/1911:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/9![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 2/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Sat 2/218:00 am
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/9![Frontier logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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.
Sat 4/44:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Thu 4/97:20 am
MIA
- ORD
Nonstop3h 30m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 3/17:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Wed 4/293:47 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$91
Best flights from Chicago to Boca RatonDiscover carefully curated flight deals from Chicago to Boca Raton that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 10, 2026.
Discover carefully curated flight deals from Chicago to Boca Raton that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 10, 2026.
This Spirit deal was found by Cheapflights users on 2/8. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Sun 3/87:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$120
This Southwest deal was found by Cheapflights users on 2/9. 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 3/107:40 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 3/176:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/9![Southwest logo]()
$131
This Delta deal was found by Cheapflights users on 2/6. 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.
Tue 3/106:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Tue 3/178:00 am
MIA
- MDW
1 stop5h 29m
Delta
Deal found 2/6![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Thu 5/147:14 am
ORD
- MIA
Nonstop3h 23m
United Airlines
Sat 5/164:15 pm
MIA
- ORD
Nonstop3h 40m
United Airlines
Deal found 2/8![United Airlines logo]()
$228
This Spirit deal was found by Cheapflights users on 2/10. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Sun 3/156:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$165
This Southwest deal was found by Cheapflights users on 2/8. 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.
Mon 3/167:30 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Wed 3/186:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/8![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 2/6. 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.
Sat 2/286:30 pm
ORD
- MIA
1 stop5h 23m
Delta
Tue 3/312:00 pm
MIA
- ORD
1 stop5h 51m
Delta
Deal found 2/6![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Thu 4/97:00 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Mon 4/138:55 am
MIA
- ORD
Nonstop3h 36m
United Airlines
Deal found 2/8![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/121:10 pm
MDW
- MIA
1 stop7h 08m
Delta
Sat 4/186:15 pm
MIA
- MDW
1 stop5h 13m
Delta
Deal found 2/8![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:35 am
MDW
- MIA
1 stop6h 33m
Delta
Wed 3/186:27 pm
MIA
- MDW
1 stop5h 04m
Delta
Deal found 2/8![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/8. 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 7/77:15 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Fri 7/104:52 pm
MIA
- ORD
1 stop8h 53m
United Airlines
Deal found 2/8![United Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 2/8. 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.
Wed 4/16:00 am
MDW
- MIA
1 stop10h 05m
Southwest
Tue 4/712:10 pm
MIA
- MDW
2 stops9h 00m
Southwest
Deal found 2/8![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 2/9. 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 3/245:30 am
ORD
- MIA
1 stop5h 39m
Delta
Tue 3/246:27 pm
MIA
- ORD
1 stop6h 27m
Delta
Deal found 2/9![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 3/187:40 am
MDW
- MIA
Nonstop3h 00m
Southwest
Tue 3/246:30 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/9![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Wed 2/2512:45 pm
ORD
- MIA
1 stop8h 14m
United Airlines
Thu 3/55:36 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 2/8![United Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 2/9. 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 3/177:10 am
ORD
- MIA
1 stop6h 00m
Delta
Tue 3/248:00 am
MIA
- ORD
1 stop6h 17m
Delta
Deal found 2/9![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/8. 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.
Mon 3/23:15 pm
MDW
- MIA
1 stop5h 40m
Southwest
Wed 3/42:35 pm
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 2/8![Southwest logo]()
$272
This United Airlines deal was found by Cheapflights users on 2/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/12:05 pm
ORD
- MIA
1 stop7h 35m
United Airlines
Fri 7/175:25 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 2/9![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 2/7. 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.
Tue 3/171:57 pm
ORD
- MIA
1 stop6h 21m
Delta
Mon 3/237:33 pm
MIA
- ORD
1 stop5h 21m
Delta
Deal found 2/7![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 2/6. 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.
Sun 3/86:07 pm
MDW
- MIA
1 stop5h 45m
Delta
Mon 3/166:27 pm
MIA
- MDW
1 stop5h 04m
Delta
Deal found 2/6![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 2/6. 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.
Tue 2/245:25 am
ORD
- MIA
1 stop5h 58m
Delta
Tue 2/244:46 pm
MIA
- ORD
1 stop8h 10m
Delta
Deal found 2/6![Delta logo]()
$277
Last-minute flights from Chicago to Boca RatonDiscover last-minute flight deals from Chicago to Boca Raton. Data last updated February 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Boca Raton. Data last updated February 10, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 2/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Sat 2/218:00 am
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/9![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Thu 2/1911:28 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/9![Frontier logo]()
$88
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:48 am
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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 2/237:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Fri 2/277:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Tue 2/247:23 pm
ORD
- MIA
Nonstop3h 16m
Multiple Airlines
Sat 2/288:00 am
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$88
This Expedia deal was found by Cheapflights users on 2/9. 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.
Tue 2/247:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Thu 2/263:50 pm
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$90
This Frontier deal was found by Cheapflights users on 2/10. 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.
Sat 2/2811:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Sat 3/77:15 am
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 2/10![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 2/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Fri 3/611:13 am
MIA
- MDW
Nonstop3h 28m
Frontier
Deal found 2/9![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sun 3/17:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Thu 3/57:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Tue 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Wed 3/47:12 am
MIA
- ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Sun 3/89:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Tue 3/176:00 am
MIA
- ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/6![Spirit Airlines logo]()
$86
This CheapOair deal was found by Cheapflights users on 2/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:05 pm
ORD
- MIA
Nonstop3h 15m
Multiple Airlines
Fri 3/136:00 am
MIA
- ORD
Nonstop3h 25m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$85
One-way flights from Chicago to Boca RatonSearch for one-way flight options from Chicago to Boca Raton. Find affordable one-way fares based on user searches. Data last updated February 10, 2026.
Search for one-way flight options from Chicago to Boca Raton. Find affordable one-way fares based on user searches. Data last updated February 10, 2026.
This Expedia deal was found by Cheapflights users on 2/7. 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.
Mon 3/29:18 am
ORD
- MIA
Nonstop3h 18m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$40
This Frontier deal was found by Cheapflights users on 2/7. 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.
Mon 3/309:42 pm
MDW
- MIA
Nonstop3h 08m
Frontier
Deal found 2/7![Frontier logo]()
$40
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Tue 3/37:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$41
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 5/157:15 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/9![Frontier logo]()
$43
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Thu 2/196:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/7![Frontier logo]()
$43
This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/10![Frontier logo]()
$44
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:48 am
ORD
- MIA
Nonstop3h 15m
Frontier
Deal found 2/9![Frontier logo]()
$45
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:15 am
MDW
- MIA
Nonstop3h 13m
Frontier
Deal found 2/9![Frontier logo]()
$45
This Expedia deal was found by Cheapflights users on 2/7. 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.
Tue 2/247:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$47
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:23 pm
ORD
- MIA
Nonstop3h 16m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$48
This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 2/10![Frontier logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sat 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 2/8![Frontier logo]()
$49
Find flight deals from Chicago to Boca Raton
Keep the following information in mind while searching for Chicago to Boca Raton flight deals. Data was last updated February 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $82 (Kiwi.com) |
One-way from | $40 (Expedia) |
Popular in | December |
Cheapest in | September |
Average price | $267 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Boca Raton that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 10, 2026.
Use the filters below to find and compare flights from Chicago to Boca Raton that are best for you.
Fly from
Chicago
Fly to
Boca Raton
Route
Depart
Return
Price
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sun 3/1
7:23 pm-11:39 pm
Nonstop3h 16m
Miami
Sun 3/8
7:12 am-9:39 am
Nonstop3h 27m
$120
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 3/10
7:40 am-11:40 am
Nonstop3h 00m
Miami
Tue 3/17
6:30 am-8:45 am
Nonstop3h 15m
$131
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sun 3/8
7:23 pm-11:39 pm
Nonstop3h 16m
Miami
Sun 3/15
6:00 am-8:25 am
Nonstop3h 25m
$165
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 3/16
7:30 pm-11:30 pm
Nonstop3h 00m
Miami
Wed 3/18
6:30 am-8:45 am
Nonstop3h 15m
$197
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 3/10
6:07 pm-12:52 am
1 stop5h 45m
Miami
Tue 3/17
8:00 am-12:29 pm
1 stop5h 29m
$217
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 2/28
6:30 pm-12:53 am
1 stop5h 23m
Miami
Tue 3/3
12:00 pm-4:51 pm
1 stop5h 51m
$217
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sun 4/12
1:10 pm-9:18 pm
1 stop7h 08m
Miami
Sat 4/18
6:15 pm-10:28 pm
1 stop5h 13m
$218
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 3/16
9:35 am-5:08 pm
1 stop6h 33m
Miami
Wed 3/18
6:27 pm-10:31 pm
1 stop5h 04m
$218
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 3/24
5:30 am-12:09 pm
1 stop5h 39m
Miami
Tue 3/24
6:27 pm-11:54 pm
1 stop6h 27m
$227
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 3/17
7:10 am-2:10 pm
1 stop6h 00m
Miami
Tue 3/24
8:00 am-1:17 pm
1 stop6h 17m
$227
Showing 1-10 of 41 results
Best time to book a flight from Chicago to Boca Raton
Have a flexible travel schedule? Discover the best time to fly to Boca Raton from Chicago with our price prediction graph.
ORD-MIA
MDW-MIA
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 Chicago to Boca Raton
CHI-BO9
ORD-MIA
MDW-MIA
How far ahead should I book a flight from Chicago to Boca Raton?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Boca Raton. Price data was last updated on February 6, 2026.
The price you pay for your flight from Chicago to Boca Raton may vary depending on when you book. For the best chance of a lower fare, look to book 41 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 Chicago to Boca Raton?
Currently, October is the cheapest month in which you can book a flight from Chicago to Boca Raton (average of $49). Flying from Chicago to Boca Raton in July is currently the most expensive (average of $118). 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 CHI to BO9?
Find hourly flight availability from Chicago to Boca Raton. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 10, 2026.
It’s typically best to fly out from Chicago to Boca Raton in the morning. Doing so could potentially save you 7% on the flight price compared to flying in the afternoon, which is usually more expensive.
What is the cheapest day to fly from Chicago to Boca Raton?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Boca Raton. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chicago to Boca Raton flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday at noon 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 Chicago to Boca Raton?
Reviews of airlines servicing Boca Raton
Get insights into the airlines that provide service to Boca Raton. 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 Boca Raton. Reviews last updated February 10, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to Boca Raton. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Boca Raton. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Boca Raton
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Boca Raton by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Boca Raton by cabin class
Find flights from Chicago to Boca Raton, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Boca Raton flights
Browse other Chicago and Boca Raton flight options. Last updated on February 10, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chicago to Boca Raton
Discover the top 8 airlines that operate flights from Chicago to Boca Raton. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$37 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$70 | Average$188 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$83 | Average$153 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$108 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$361 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$314 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$364 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% |