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Boca Raton

$69+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Boca Raton are usually found in September or July, booked 41 days in advance, depart on a Thursday or Tuesday and return on a Thursday

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 June 16, 2025.

Round-trip from

$136
(Cheapflightsfares)

One-way from

$69
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$276
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. 12% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/13. 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 7/128:09 amORD - MIA
Nonstop3h 14mSpirit Airlines
Thu 7/171:35 pmMIA - ORD
Nonstop3h 36mSpirit Airlines
Deal found 6/13$136
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/212:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Mon 8/2512:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 6/15$137
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/81:43 pmORD - MIA
Nonstop3h 17mMultiple Airlines
Thu 7/103:00 pmMIA - ORD
1 stop10h 22mMultiple Airlines
Deal found 6/14$139
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/146:00 amORD - MIA
Nonstop3h 08mAmerican Airlines
Tue 8/198:10 pmMIA - ORD
Nonstop3h 31mAmerican Airlines
Deal found 6/14$147
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/71:30 pmORD - MIA
1 stop8h 35mSouthwest
Tue 8/127:10 amMIA - ORD
1 stop5h 40mSouthwest
Deal found 6/15$177
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/15:01 amORD - MIA
1 stop5h 27mFrontier
Fri 7/412:20 pmMIA - ORD
1 stop5h 38mFrontier
Deal found 6/14$188
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1910:03 pmMDW - MIA
Nonstop3h 00mFrontier
Sun 10/266:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 6/14$193
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/192:00 pmORD - MIA
1 stop7h 45mDelta
Thu 7/247:23 pmMIA - ORD
1 stop5h 46mDelta
Deal found 6/14$217
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:00 amMDW - MIA
1 stop7h 50mDelta
Tue 8/512:46 pmMIA - MDW
1 stop6h 54mDelta
Deal found 6/14$217
This United Airlines deal was found by Cheapflights users on 6/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/410:50 amORD - MIA
Nonstop3h 20mUnited Airlines
Fri 7/114:16 pmMIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 6/15$240

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 June 16, 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 7/12

8:09 am-12:23 pm

Nonstop3h 14m

Miami

Thu 7/17

1:35 pm-4:11 pm

Nonstop3h 36m

$136

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 8/21

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Mon 8/25

12:35 pm-2:45 pm

Nonstop3h 10m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/8

1:43 pm-6:00 pm

Nonstop3h 17m

Miami

Thu 7/10

3:00 pm-12:22 am

1 stop10h 22m

$139

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 8/14

6:00 am-10:08 am

Nonstop3h 08m

Miami

Tue 8/19

8:10 pm-10:41 pm

Nonstop3h 31m

$147

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 8/7

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Tue 8/12

7:10 am-11:50 am

1 stop5h 40m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/1

5:01 am-11:28 am

1 stop5h 27m

Miami

Fri 7/4

12:20 pm-4:58 pm

1 stop5h 38m

$188

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/19

2:00 pm-10:45 pm

1 stop7h 45m

Miami

Thu 7/24

7:23 pm-12:09 am

1 stop5h 46m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 7/29

6:00 am-2:50 pm

1 stop7h 50m

Miami

Tue 8/5

12:46 pm-6:40 pm

1 stop6h 54m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 7/4

10:50 am-3:10 pm

Nonstop3h 20m

Miami

Fri 7/11

4:16 pm-6:50 pm

Nonstop3h 34m

$240

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/11

6:15 am-11:52 pm

1 stop16h 37m

Miami

Sun 9/14

6:42 pm-11:25 pm

1 stop5h 43m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 21 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 June 13, 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 $228). 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 June 16, 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 Tuesday evenings when fares are most often at their lowest. Tuesday 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 June 16, 2025.

The most flights from CHI to BO9 are scheduled on a Saturday (47 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (43 on average).

Rainfall in Boca Raton by month

Plan your trip to Boca Raton by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boca Raton ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Boca Raton when rainfall is around 1.6 in.

Temperature in Boca Raton by month

Plan your trip to Boca Raton by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boca Raton, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 June 16, 2025.
To help decide which airline to fly from Chicago to Boca Raton, see what other customers have to say about Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $69 on United Airlines. Other airlines that offer cheap prices include Southwest from $69 and American Airlines from $70 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: ANA (91%), Finnair (88%), Air Canada( 87%).

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

    On average you can expect to pay $639 for a flight from Chicago to Boca Raton. The cheapest flight overall is $64 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $106.

  • 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 $228). 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$172FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$77Average$189FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$134Average$381FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$350FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
DeltaCheapest$177Average$345FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$193Average$395FlexibilityNo cancel feeOn-time63%

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