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Delray Beach

$66+ Cheap flights from Chicago (CHI) to Delray Beach, 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 Delray Beach 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 Delray Beach

Keep the following information in mind while searching for Chicago to Delray Beach 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 Delray Beach
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One-way flight from Chicago (CHI) to Delray Beach
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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 Delray Beach

Cheapest flights from Chicago to Delray Beach
Explore the most affordable flight options available from Chicago to Delray Beach. 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 Delray Beach 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 Delray Beach that are best for you.

Fly from

Chicago

Fly to

Delray Beach

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 Delray Beach

Have a flexible travel schedule? Discover the best time to fly to Delray Beach 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 Delray Beach

How far ahead should I book a flight from Chicago to Delray Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Delray Beach. Price data was last updated on April 25, 2025.

The best time to book flights from Chicago to Delray Beach is 39 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Delray Beach?

Currently, September is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $228). Flying from Chicago to Delray Beach 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 DB9?

Find hourly flight availability from Chicago to Delray Beach. 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.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Delray Beach as you normally would.

What is the cheapest day to fly from Chicago to Delray Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Delray Beach. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Delray Beach 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 Delray Beach

Explore weekly flight availability from Chicago to Delray Beach. 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 DB9 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 Delray Beach by month

Plan your trip to Delray Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Delray Beach 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 Delray Beach when rainfall is around 1.6 in.

Temperature in Delray Beach by month

Plan your trip to Delray Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Delray Beach, 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 Delray Beach

Get insights into the airlines that provide service to Delray Beach. 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 Delray Beach. Reviews last updated May 1, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Delray Beach to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

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 Delray Beach. 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 Delray Beach one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $66. Users have also found prices from $85 and $90 on Frontier and American Airlines, respectively.

  • What are the most reliable airlines from Chicago to Delray Beach?

    No one likes to see their flight delayed. When booking a flight from Chicago to Delray Beach consider choosing Avianca (84%), Spirit Airlines (84%) or Air New Zealand (81%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Delray Beach?

    Looking for the cheapest flight from Chicago to Delray Beach? While on average our users pay $727, our data indicates the cheapest price to be $57. The most popular route (Chicago O'Hare Intl - Miami), is priced around $75.

  • Can I find deals for flights from Chicago to Delray Beach that include hotel bookings?

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

  • How can I find direct flights from Chicago to Delray Beach?

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

  • Can I find deals for business class flights from Chicago to Delray Beach?

    Yes. Cheapflights offers flight deals from Chicago to Delray Beach 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 Delray Beach?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $228). Flying from Chicago to Delray Beach 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 Delray Beach

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 Delray Beach

Discover the top 6 airlines that operate flights from Chicago to Delray Beach. 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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