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Boca Raton

$67+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Boca Raton are usually found in September or August, booked 41 days in advance, depart on a Thursday or Friday 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 August 1, 2025.

Round-trip from

$133
(FlightHub)

One-way from

$67
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$204
From Chicago (CHI) to Boca Raton
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One-way flight from Chicago (CHI) to Boca Raton
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Highest demand for flights based on searches. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 1, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:12 amORD - MIA
1 stop11h 05mSpirit Airlines
Thu 9/117:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 7/31$133
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/67:05 amORD - MIA
Nonstop3h 04mAmerican Airlines
Mon 9/87:00 pmMIA - ORD
Nonstop3h 22mAmerican Airlines
Deal found 7/31$137
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/82:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Sat 9/134:05 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 7/31$137
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 10/276:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 7/30$151
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:30 pmORD - MIA
1 stop8h 35mSouthwest
Sun 9/147:15 amMIA - ORD
1 stop5h 35mSouthwest
Deal found 7/31$157
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/307:00 amORD - MIA
1 stop22h 30mMultiple Airlines
Mon 9/87:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 7/30$160
This Delta deal was found by Cheapflights users on 7/29. 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 9/134:31 pmMDW - MIA
1 stop6h 52mDelta
Sat 9/208:10 amMIA - MDW
1 stop5h 18mDelta
Deal found 7/29$217

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 August 1, 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

Sat 9/6

11:12 am-11:17 pm

1 stop11h 05m

Miami

Thu 9/11

7:00 am-9:18 am

Nonstop3h 18m

$133

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sat 9/13

4:05 pm-6:15 pm

Nonstop3h 10m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

7:05 am-11:09 am

Nonstop3h 04m

Miami

Mon 9/8

7:00 pm-9:22 pm

Nonstop3h 22m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$151

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/12

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Sun 9/14

7:15 am-11:50 am

1 stop5h 35m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/30

7:00 am-6:30 am

1 stop22h 30m

Miami

Mon 9/8

7:00 am-9:18 am

Nonstop3h 18m

$160

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/13

4:31 pm-12:23 am

1 stop6h 52m

Miami

Sat 9/20

8:10 am-12:28 pm

1 stop5h 18m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 9/7

10:27 am-2:39 pm

Nonstop3h 12m

$67

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/6

9:20 am-1:20 pm

Nonstop3h 00m

$69

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/1

5:00 am-9:02 am

Nonstop3h 02m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 results
1
2

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 July 25, 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, 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 August 1, 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 August 1, 2025.

The most flights from CHI to BO9 are scheduled on a Thursday (43 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (28 on average).

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 August 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

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.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

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
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

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
8,049 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

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
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

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.

  • 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 $67 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $69 and Southwest from $69 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 (84%), Air Canada (84%), Copa Airlines( 84%).

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

    On average you can expect to pay $750 for a flight from Chicago to Boca Raton. The cheapest flight overall is $57 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

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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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$199FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$371FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$345FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$176Average$387FlexibilityNo cancel feeOn-time63%
DeltaCheapest$177Average$348FlexibilityNo cancel feeOn-timeN/A

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