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Boca Raton

$66+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Boca Raton are usually found in July or September, booked 39 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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$136
(Cheapflightsfares)

One-way from

$66
(eDestinos)

Popular in

December

Cheapest in

July

Average price

$208
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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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. 13% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/179:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Sat 5/243:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 4/30$136
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Mon 6/29:55 amORD - MIA
Nonstop3h 15mMultiple Airlines
Sun 6/85:30 amMIA - ORD
1 stop5h 52mMultiple Airlines
Deal found 4/30$150
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/46:55 amORD - MIA
1 stop4h 45mAmerican Airlines
Wed 6/42:18 pmMIA - ORD
1 stop6h 17mAmerican Airlines
Deal found 4/30$184
This Southwest deal was found by Cheapflights users on 4/30. 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 6/45:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Sat 6/75:45 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 4/30$197
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 11/83:59 pmMDW - MIA
Nonstop3h 02mFrontier
Sat 11/1512:47 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 4/30$212
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/216:15 pmORD - MIA
1 stop5h 42mDelta
Tue 6/245:30 amMIA - ORD
1 stop5h 39mDelta
Deal found 4/30$217
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:15 pmMDW - MIA
1 stop7h 22mDelta
Sat 5/315:35 amMIA - MDW
1 stop5h 05mDelta
Deal found 4/30$217
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:00 amORD - MIA
1 stop8h 00mFrontier
Thu 5/156:00 amMIA - ORD
1 stop8h 34mFrontier
Deal found 4/30$218

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 May 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 5/17

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Sat 5/24

3:15 pm-5:41 pm

Nonstop3h 26m

$136

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 6/2

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Sun 6/8

5:30 am-10:22 am

1 stop5h 52m

$150

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 6/4

6:55 am-12:40 pm

1 stop4h 45m

Miami

Wed 6/4

2:18 pm-7:35 pm

1 stop6h 17m

$184

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 6/4

5:10 pm-9:05 pm

Nonstop2h 55m

Miami

Sat 6/7

5:45 am-7:50 am

Nonstop3h 05m

$197

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 6/21

6:15 pm-12:57 am

1 stop5h 42m

Miami

Tue 6/24

5:30 am-10:09 am

1 stop5h 39m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/24

4:15 pm-12:37 am

1 stop7h 22m

Miami

Sat 5/31

5:35 am-9:40 am

1 stop5h 05m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 6/5

2:58 pm-11:50 pm

1 stop7h 52m

Miami

Mon 6/9

7:25 am-8:56 pm

1 stop14h 31m

$218

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/31

6:10 am-10:09 pm

1 stop14h 59m

Miami

Sun 6/1

10:59 pm-10:16 pm

1 stop24h 17m

$260

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/14

12:40 pm-9:30 pm

1 stop7h 50m

Miami

Sat 5/17

6:50 am-4:45 pm

2 stops10h 55m

$278

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 5/20

9:14 pm-9:34 am

1 stop11h 20m

$66

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 22 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 April 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 39 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 May 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 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 May 1, 2025.

The most flights from CHI to BO9 are scheduled on a Thursday (45 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 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 May 1, 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
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
4,293 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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 $66 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $85 and American Airlines from $90 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: Avianca (84%), Spirit Airlines (84%), Air New Zealand( 81%).

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

    On average you can expect to pay $727 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 $75.

  • 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.

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Alternative routes for Chicago to Boca Raton

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Boca Raton

Discover the top 6 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$165FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$179FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$159Average$353FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$177Average$354FlexibilityNo cancel feeOn-time69%
DeltaCheapest$177Average$371FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$203Average$398FlexibilityNo cancel feeOn-time63%

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