HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boca Raton

$61+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 51 days in advance, depart on a Thursday or Monday and return on a Friday

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 September 17, 2025.

Round-trip from

$104
(Kiwi.com)

One-way from

$61
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$231
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 September 2025
Search Deals

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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sun 11/27:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/16$104
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/610:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sat 10/116:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/16$105
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sun 10/127:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/15$107
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/31:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Fri 12/1210:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/15$108
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/81:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Tue 12/910:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/15$109
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Mon 10/610:27 amORD - MIA
Nonstop3h 02mMultiple Airlines
Thu 10/94:49 pmMIA - ORD
1 stop9h 19mMultiple Airlines
Deal found 9/15$110
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/110:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Sat 10/47:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/16$112
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/46:30 amMDW - MIA
Nonstop3h 17mFrontier
Sat 12/1311:42 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 9/16$113
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/510:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Thu 10/167:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/14$113
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:18 pmMDW - MIA
Nonstop3h 01mFrontier
Sat 10/2510:34 amMIA - MDW
1 stop7h 39mFrontier
Deal found 9/15$114
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Sat 10/111:14 pmORD - MIA
1 stop9h 29mMultiple Airlines
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 9/15$116
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/110:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Thu 10/97:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/15$117

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 September 17, 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

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 10/3

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Sun 10/5

7:00 am-9:22 am

Nonstop3h 22m

$148

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 10/22

6:00 am-2:17 pm

1 stop7h 17m

Miami

Wed 10/29

7:00 am-9:29 am

Nonstop3h 29m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/2

10:35 am-6:57 pm

1 stop7h 22m

Miami

Tue 2/10

6:00 am-12:01 pm

1 stop7h 01m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 11/15

1:45 pm-9:40 pm

2 stops6h 55m

Miami

Sun 12/7

6:55 am-11:10 am

1 stop5h 15m

$222

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 10/3

10:54 am-3:11 pm

Nonstop3h 17m

Miami

Tue 10/7

4:17 pm-6:47 pm

Nonstop3h 30m

$222

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 12/6

6:22 pm-12:46 am

1 stop5h 24m

Miami

Thu 12/18

8:05 am-1:51 pm

1 stop6h 46m

$227

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/6

9:50 am-4:10 pm

1 stop5h 20m

Miami

Sat 1/17

4:30 pm-6:45 pm

Nonstop3h 15m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 12/16

2:32 pm-9:42 pm

1 stop6h 10m

Miami

Tue 12/23

6:23 pm-11:58 pm

1 stop6h 35m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 11/24

9:46 am-3:47 pm

1 stop5h 01m

Miami

Thu 12/4

12:00 pm-4:18 pm

1 stop5h 18m

$227

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 9/30

12:43 pm-6:33 pm

1 stop4h 50m

Miami

Wed 10/8

6:00 am-9:40 am

1 stop4h 40m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 43 results
1
2
3
...
5

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 September 12, 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 51 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, September is the cheapest month in which you can book a flight from Chicago to Boca Raton (average of $232). Flying from Chicago to Boca Raton in March is currently the most expensive (average of $289). 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 September 17, 2025.

When flying from Chicago to Boca Raton, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 Monday evenings when fares are most often at their lowest. Wednesday afternoons 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 September 17, 2025.

The most flights from CHI to BO9 are scheduled on a Monday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 September 17, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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 12m. The distance from Chicago to Boca Raton is about 1198 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 $72 on Frontier. Other airlines that offer cheap prices include Southwest from $90 and Delta from $109 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: Emirates (88%), United Airlines (86%), Spirit Airlines( 82%).

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

    On average you can expect to pay $601 for a flight from Chicago to Boca Raton. The cheapest flight overall is $60 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $85.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Boca Raton (average of $232). Flying from Chicago to Boca Raton in March is currently the most expensive (average of $289). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Boca Raton

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
Midway to Miami flights
Midway to Tampa flights
Midway to Fort Lauderdale flights
O'Hare Intl to Sarasota flights
St. Louis to Orlando flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Key West flights
St. Louis to Miami flights
Midway to Fort Myers flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
O'Hare Intl to Panama City flights
St. Louis to Tampa flights
Midway to Sarasota flights
Midway to Jacksonville flights
St. Louis to Fort Lauderdale flights
St. Louis to Fort Myers flights
Moline to Orlando flights
St. Louis to Jacksonville flights
Midway to Key West flights
St. Louis to Key West flights
Peoria to Orlando flights
Midway to Panama City flights
St. Louis to Sarasota flights
Midway to Pensacola flights
Rockford to Orlando Sanford Intl flights
Moline to Tampa flights
St. Louis to West Palm Beach flights
O'Hare Intl to Daytona Beach flights
Rockford to St Petersburg flights
St. Louis to Panama City flights
O'Hare Intl to Tallahassee flights
Peoria to Fort Myers flights
O'Hare Intl to Melbourne flights
Bloomington to Orlando flights
Moline to Miami flights
Peoria to Tampa flights
O'Hare Intl to Valparaiso flights
St. Louis to Pensacola flights
Midway to Daytona Beach flights
Moline to Pensacola flights
O'Hare Intl to Gainesville flights
Peoria to Fort Lauderdale flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$172FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$203FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$352FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$323FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$347FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$176Average$388FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.