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Boca Raton

$56+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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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 Thursday and return on a Friday

Find flight deals from Chicago to Boca Raton

Cheapest flights from Chicago to Boca Raton
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 November 2, 2025.

This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:57 pmMDW - MIA
Nonstop3h 06mFrontier
Sat 12/68:09 pmMIA - MDW
Nonstop3h 21mFrontier
Deal found 11/1$108
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:39 pmORD - MIA
1 stop5h 51mMultiple Airlines
Wed 1/72:35 pmMIA - ORD
Nonstop3h 25mMultiple Airlines
Deal found 11/1$109
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:11 amORD - MIA
1 stop8h 28mFrontier
Sat 12/132:13 pmMIA - ORD
1 stop21h 18mFrontier
Deal found 11/1$110
This Priceline deal was found by Cheapflights users on 10/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:05 amMDW - MIA
1 stop10h 04mFrontier
Sat 11/222:44 pmMIA - MDW
Nonstop3h 13mFrontier
Deal found 10/31$111
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:01 pmORD - MIA
1 stop6h 30mSpirit Airlines
Fri 12/54:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/1$111
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/265:57 pmMDW - MIA
Nonstop3h 06mFrontier
Tue 12/25:58 pmMIA - MDW
1 stop15h 48mFrontier
Deal found 11/1$112
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/111:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Fri 12/54:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/1$112
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:44 amMDW - MIA
1 stop11h 03mFrontier
Sat 12/138:09 pmMIA - MDW
Nonstop3h 21mFrontier
Deal found 10/31$113
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Wed 11/265:57 pmMDW - MIA
Nonstop3h 06mFrontier
Thu 11/2711:55 amMIA - MDW
1 stop11h 48mFrontier
Deal found 10/30$114
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:59 pmMDW - MIA
Nonstop3h 10mFrontier
Mon 12/85:30 amMIA - MDW
1 stop5h 22mFrontier
Deal found 11/1$115
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/3011:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Sat 12/64:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/2$115
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sat 12/69:14 pmORD - MIA
1 stop10h 09mSpirit Airlines
Thu 12/182:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$116

Cheap 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 November 2, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$108
(CheapOair)

One-way from

$56
(eDestinos)

Popular in

March

Cheapest in

September

Average price

$292
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
Search Deals
From Chicago (CHI) to Boca Raton
Search Deals
One-way flight from Chicago (CHI) to Boca Raton
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 2, 2025.
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

MDW - MIA

MDWMIA

Chicago Midway

Tue 12/9

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Wed 12/10

1:05 pm-3:20 pm

Nonstop3h 15m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 12/4

12:39 pm-4:50 pm

Nonstop3h 11m

Miami

Thu 12/11

12:23 pm-2:52 pm

Nonstop3h 29m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 1/25

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Sat 1/31

5:05 pm-10:10 pm

1 stop6h 05m

$167

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 12/3

12:50 pm-6:26 pm

1 stop4h 36m

Miami

Tue 12/9

6:00 am-9:54 am

1 stop4h 54m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 1/7

11:21 am-5:15 pm

1 stop4h 54m

Miami

Sat 1/10

8:05 am-12:48 pm

1 stop5h 43m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 12/5

5:59 pm-12:46 am

1 stop5h 47m

Miami

Wed 12/10

12:36 pm-4:48 pm

1 stop5h 12m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/13

1:45 pm-8:05 pm

1 stop5h 20m

Miami

Sat 1/17

6:45 am-11:10 am

1 stop5h 25m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/9

5:55 pm-12:51 am

1 stop5h 56m

Miami

Sat 1/17

8:05 am-1:07 pm

1 stop6h 02m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 12/2

1:20 pm-8:51 pm

1 stop6h 31m

Miami

Wed 12/3

10:43 am-3:20 pm

1 stop5h 37m

$218

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 12/4

12:39 pm-4:50 pm

Nonstop3h 11m

Miami

Mon 12/8

5:56 pm-8:25 pm

Nonstop3h 29m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 41 results
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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.
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

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 October 31, 2025.

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, February is the cheapest month in which you can book a flight from Chicago to Boca Raton (average of $47). Flying from Chicago to Boca Raton in June is currently the most expensive (average of $117). 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 November 2, 2025.

It’s typically best to fly out from Chicago to Boca Raton in the morning. Doing so could potentially save you 13% 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 December 16, 2024.

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. Sunday evenings 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 November 2, 2025.
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.
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
11,034 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,120 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,118 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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.

  • How long is the flight from Chicago to Boca Raton?

    Departing from Chicago to Boca Raton will take you 3h 05m. The distance from Chicago to Boca Raton is about 1183 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Boca Raton one-way?

    One-way options have recently been found by users for as low as $59 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $69 and Southwest from $79 one-way.

  • What are the most reliable airlines from Chicago to Boca Raton?

    Before booking your flight to Boca Raton from Chicago, check out the most reliable airlines to get you to your destination on time: Spirit Airlines (88%), United Airlines (86%), Alaska Airlines( 82%).

  • What are the cheapest flights from Chicago to Boca Raton?

    On average you can expect to pay $655 for a flight from Chicago to Boca Raton. The cheapest flight overall is $59 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $63.

  • Can I find deals for flights from Chicago to Boca Raton that include hotel bookings?

    Yes. In addition to deals on Chicago to Boca Raton flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Boca Raton?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boca Raton.

  • Can I find deals for business class flights from Chicago to Boca Raton?

    Yes. Cheapflights offers flight deals from Chicago to Boca Raton by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Boca Raton?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Boca Raton (average of $47). Flying from Chicago to Boca Raton in June is currently the most expensive (average of $117). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from Chicago to Boca Raton

Discover the top 7 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$187FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$200FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$371FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$153Average$343FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$422FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$355FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%

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