$48+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Apr 30 — May 71
Round-trip
1 adult, Economy
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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 October, booked 41 days in advance, depart on a Monday or Sunday and return on a Friday
Cheap flight deals from Chicago to Boca Raton
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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 March 31, 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 March 31, 2026.
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Fri 4/1011:35 am
MIA
- MDW
Nonstop3h 26m
Frontier
Deal found 3/31![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:55 am
ORD
- MIA
Nonstop3h 05m
Multiple Airlines
Thu 4/169:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:55 am
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Fri 4/2410:41 am
MIA
- ORD
Nonstop3h 24m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$101
This Trip.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/2211:10 am
MIA
- MDW
1 stop9h 21m
Frontier
Deal found 3/29![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Thu 4/306:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$102
This Priceline deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:51 pm
ORD
- MIA
Nonstop3h 06m
Multiple Airlines
Thu 4/912:04 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 3/27![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/44:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Tue 4/147:20 am
MIA
- ORD
Nonstop3h 30m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$105
This Expedia deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Wed 4/296:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$106
This WAYA deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Wed 4/223:54 pm
MIA
- MDW
1 stop7h 20m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/1611:28 am
ORD
- MIA
1 stop10h 03m
Spirit Airlines
Sat 4/1811:37 am
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$107
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Wed 4/226:30 am
MIA
- ORD
1 stop11h 41m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$108
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 March 31, 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 March 31, 2026.
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Mon 5/186:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/30![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:10 pm
MDW
- MIA
1 stop6h 33m
Delta
Mon 5/186:00 am
MIA
- MDW
1 stop6h 56m
Delta
Deal found 3/29![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3110:40 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Tue 6/212:30 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 3/30![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:05 pm
MDW
- MIA
2 stops9h 00m
Southwest
Sat 5/26:15 am
MIA
- MDW
2 stops7h 00m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:40 pm
ORD
- MIA
2 stops6h 20m
Southwest
Sat 5/96:35 am
MIA
- ORD
2 stops9h 55m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:10 am
MDW
- MIA
1 stop6h 50m
Southwest
Sat 5/97:00 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/30![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:45 pm
MDW
- MIA
Nonstop3h 00m
Southwest
Thu 5/147:15 pm
MIA
- MDW
1 stop5h 15m
Southwest
Deal found 3/27![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:00 am
ORD
- MIA
Nonstop3h 22m
United Airlines
Wed 4/154:18 pm
MIA
- ORD
Nonstop3h 39m
United Airlines
Deal found 3/26![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/182:15 pm
MDW
- MIA
1 stop5h 05m
Southwest
Mon 4/206:05 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/26![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sun 5/36:45 am
MIA
- MDW
Nonstop3h 10m
Southwest
Deal found 3/29![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:40 am
ORD
- MIA
Nonstop3h 24m
United Airlines
Sun 5/314:06 pm
MIA
- ORD
Nonstop3h 43m
United Airlines
Deal found 3/27![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:35 pm
ORD
- MIA
1 stop6h 57m
Delta
Fri 9/183:45 pm
MIA
- ORD
1 stop7h 58m
Delta
Deal found 3/28![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:55 am
MDW
- MIA
Nonstop3h 00m
Southwest
Sat 5/307:00 am
MIA
- MDW
Nonstop3h 15m
Southwest
Deal found 3/28![Southwest logo]()
$269
This United Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:30 am
ORD
- MIA
1 stop9h 17m
United Airlines
Mon 6/15:24 pm
MIA
- ORD
Nonstop3h 44m
United Airlines
Deal found 3/27![United Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:15 am
MDW
- MIA
1 stop7h 35m
Southwest
Sat 5/236:35 am
MIA
- MDW
2 stops9h 05m
Southwest
Deal found 3/30![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:55 am
ORD
- MIA
2 stops14h 15m
Southwest
Fri 5/156:20 am
MIA
- ORD
2 stops7h 30m
Southwest
Deal found 3/27![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:40 pm
ORD
- MIA
2 stops6h 20m
Southwest
Mon 4/276:20 am
MIA
- ORD
2 stops7h 30m
Southwest
Deal found 3/29![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:55 am
ORD
- MIA
2 stops14h 15m
Southwest
Sat 5/236:15 am
MIA
- ORD
2 stops10h 15m
Southwest
Deal found 3/30![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:05 pm
ORD
- MIA
1 stop5h 55m
Southwest
Mon 4/205:30 am
MIA
- ORD
2 stops11h 00m
Southwest
Deal found 3/26![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:35 pm
ORD
- MIA
2 stops17h 45m
Southwest
Mon 6/16:20 am
MIA
- ORD
2 stops7h 30m
Southwest
Deal found 3/27![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/133:05 pm
ORD
- MIA
1 stop5h 55m
Southwest
Fri 4/176:20 am
MIA
- ORD
2 stops7h 30m
Southwest
Deal found 3/30![Southwest logo]()
$466
Last-minute flights from Chicago to Boca RatonDiscover last-minute flight deals from Chicago to Boca Raton. Data last updated March 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Boca Raton. Data last updated March 31, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/44:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Tue 4/147:20 am
MIA
- ORD
Nonstop3h 30m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$105
This Priceline deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:51 pm
ORD
- MIA
Nonstop3h 06m
Multiple Airlines
Thu 4/912:04 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:55 am
ORD
- MIA
Nonstop3h 05m
Multiple Airlines
Thu 4/169:21 pm
MIA
- ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:55 am
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Fri 4/2410:41 am
MIA
- ORD
Nonstop3h 24m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$101
This Trip.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Wed 4/2211:10 am
MIA
- MDW
1 stop9h 21m
Frontier
Deal found 3/29![Frontier logo]()
$101
This WAYA deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- MIA
Nonstop3h 10m
Multiple Airlines
Wed 4/223:54 pm
MIA
- MDW
1 stop7h 20m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/1611:28 am
ORD
- MIA
1 stop10h 03m
Spirit Airlines
Sat 4/1811:37 am
MIA
- ORD
Nonstop3h 28m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$107
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Wed 4/226:30 am
MIA
- ORD
1 stop11h 41m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$108
This CheapOair deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Thu 4/306:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Thu 4/309:21 pm
MIA
- ORD
Nonstop3h 38m
Frontier
Deal found 3/27![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Wed 4/296:30 am
MIA
- ORD
1 stop11h 41m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- MIA
Nonstop3h 19m
Multiple Airlines
Tue 4/287:04 pm
MIA
- ORD
1 stop16h 19m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$109
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 March 31, 2026.
Search for one-way flight options from Chicago to Boca Raton. Find affordable one-way fares based on user searches. Data last updated March 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:28 am
ORD
- MIA
1 stop10h 03m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$48
This Frontier deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/29![Frontier logo]()
$49
This Super.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/57:25 am
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/27![Frontier logo]()
$49
This CheapOair deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/26![Frontier logo]()
$50
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/167:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$50
This Expedia deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:50 am
ORD
- MIA
Nonstop3h 08m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$51
This Cheapflightsfares deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 3/26![Spirit Airlines logo]()
$54
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/46:30 am
MDW
- MIA
Nonstop3h 10m
Frontier
Deal found 3/31![Frontier logo]()
$55
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:51 pm
ORD
- MIA
Nonstop3h 06m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$55
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:52 pm
ORD
- MIA
Nonstop3h 19m
Frontier
Deal found 3/30![Frontier logo]()
$56
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/149:45 am
ORD
- MIA
1 stop9h 59m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$57
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/29:16 am
ORD
- MIA
1 stop5h 48m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$59
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 March 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $100 (Cheapflightsfares) |
One-way from | $48 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $318 |
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 March 31, 2026.
Use the filters below to find and compare flights from Chicago to Boca Raton that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 4/21
7:55 am-11:55 am
Nonstop3h 00m
Miami
Mon 5/18
6:05 am-8:20 am
Nonstop3h 15m
$210
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 4/25
12:05 pm-10:05 pm
2 stops9h 00m
Miami
Sat 5/2
6:15 am-12:15 pm
2 stops7h 00m
$227
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 5/4
2:40 pm-10:00 pm
2 stops6h 20m
Miami
Sat 5/9
6:35 am-3:30 pm
2 stops9h 55m
$227
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/2
9:10 am-5:00 pm
1 stop6h 50m
Miami
Sat 5/9
7:00 am-9:15 am
Nonstop3h 15m
$231
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/16
5:10 pm-12:43 am
1 stop6h 33m
Miami
Mon 5/18
6:00 am-11:56 am
1 stop6h 56m
$239
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sun 5/10
6:45 pm-10:45 pm
Nonstop3h 00m
Miami
Thu 5/14
7:15 pm-11:30 pm
1 stop5h 15m
$249
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 4/18
2:15 pm-8:20 pm
1 stop5h 05m
Miami
Mon 4/20
6:05 am-8:20 am
Nonstop3h 15m
$257
Quickest round-trip
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 4/29
7:55 am-11:55 am
Nonstop3h 00m
Miami
Sun 5/3
6:45 am-8:55 am
Nonstop3h 10m
$259
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 5/26
7:55 am-11:55 am
Nonstop3h 00m
Miami
Sat 5/30
7:00 am-9:15 am
Nonstop3h 15m
$269
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 5/20
8:15 am-4:50 pm
1 stop7h 35m
Miami
Sat 5/23
6:35 am-2:40 pm
2 stops9h 05m
$309
Showing 1-10 of 45 resultsSorted by cheapest first
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.
MDW-MIA
ORD-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
MDW-MIA
ORD-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 March 13, 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 March 31, 2026.
It’s typically best to fly out from Chicago to Boca Raton at noon. Doing so could potentially save you 14% 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 March 28, 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. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Boca Raton
Explore weekly flight availability from Chicago to Boca Raton. 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 March 31, 2026.
The most flights from CHI to BO9 are scheduled on a Monday (60 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (39 on average).
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 March 31, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Boca Raton
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Complete your trip
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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 March 31, 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 March 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chicago to Boca Raton
Discover the top 9 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 March 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$40 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$70 | Average$193 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$147 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$89 | Average$260 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$311 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$358 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$341 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$173 | Average$368 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% |