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Delray Beach

$69+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Delray Beach are usually found in September or July, booked 41 days in advance, depart on a Thursday or Tuesday and return on a Wednesday

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 July 3, 2025.

Round-trip from

$129
(Booking.com)

One-way from

$69
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$185
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. 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 July 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 July 3, 2025.

This Booking.com deal was found by Cheapflights users on 7/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1610:27 amORD - MIA
Nonstop3h 22mSpirit Airlines
Sat 8/237:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 7/2$129
This Expedia deal was found by Cheapflights users on 7/3. 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 Expedia 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 7/3$129
This FlightHub deal was found by Cheapflights users on 7/2. 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.
Fri 8/2211:44 amORD - MIA
1 stop17h 46mMultiple Airlines
Tue 8/267:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 7/2$134
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/307:05 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Fri 9/123:50 pmMIA - ORD
Nonstop3h 23mAmerican Airlines
Deal found 7/2$137
This Southwest deal was found by Cheapflights users on 7/3. 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.
Sat 8/239:20 amMDW - MIA
Nonstop3h 00mSouthwest
Sun 8/247:30 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 7/3$137
This Priceline deal was found by Cheapflights users on 7/2. 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.
Thu 7/315:01 amORD - MIA
1 stop5h 13mFrontier
Sun 8/33:00 pmMIA - ORD
1 stop10h 22mFrontier
Deal found 7/2$142
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 8/107:01 amORD - MIA
Nonstop3h 17mUnited Airlines
Wed 8/1312:20 pmMIA - ORD
Nonstop3h 35mUnited Airlines
Deal found 7/2$153
This Southwest deal was found by Cheapflights users on 7/3. 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.
Sun 8/247:30 amORD - MIA
1 stop7h 35mSouthwest
Wed 8/276:55 amMIA - ORD
1 stop7h 10mSouthwest
Deal found 7/3$157

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 July 3, 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 8/16

10:27 am-2:49 pm

Nonstop3h 22m

Miami

Sat 8/23

7:00 am-9:22 am

Nonstop3h 22m

$129

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 8/22

11:44 am-6:30 am

1 stop17h 46m

Miami

Tue 8/26

7:00 am-9:22 am

Nonstop3h 22m

$134

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/30

7:05 pm-11:24 pm

Nonstop3h 19m

Miami

Fri 9/12

3:50 pm-6:13 pm

Nonstop3h 23m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 8/23

9:20 am-1:20 pm

Nonstop3h 00m

Miami

Sun 8/24

7:30 am-9:35 am

Nonstop3h 05m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 8/13

2:48 pm-10:34 pm

1 stop6h 46m

Miami

Mon 8/18

3:00 pm-11:17 pm

1 stop9h 17m

$139

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 7/31

5:01 am-11:14 am

1 stop5h 13m

Miami

Sun 8/3

3:00 pm-12:22 am

1 stop10h 22m

$142

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 8/10

7:01 am-11:18 am

Nonstop3h 17m

Miami

Wed 8/13

12:20 pm-2:55 pm

Nonstop3h 35m

$153

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 8/24

7:30 am-4:05 pm

1 stop7h 35m

Miami

Wed 8/27

6:55 am-1:05 pm

1 stop7h 10m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 9/7

5:00 am-9:04 am

Nonstop3h 04m

$69

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/1

2:10 pm-6:10 pm

Nonstop3h 00m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 17 results
1
2

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 June 27, 2025.

The best time to book flights from Chicago to Delray Beach is 41 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 $231). 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 July 3, 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 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 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 July 3, 2025.

The most flights from CHI to DB9 are scheduled on a Thursday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

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 July 3, 2025.
Read through reviews of airlines operating flights from Chicago to Delray Beach, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
8,086 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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 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 American Airlines. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $70 on Southwest and Frontier, 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 Air Canada (87%), Copa Airlines (87%) or Air New Zealand (87%) 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 $684, our data indicates the cheapest price to be $71. The most popular route (Chicago O'Hare Intl - Miami), is priced around $87.

  • 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 $231). 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.

See more FAQs

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Top 7 airlines flying from Chicago to Delray Beach

Discover the top 7 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$173FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$80Average$195FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$129Average$381FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$161Average$348FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
DeltaCheapest$177Average$351FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$195Average$394FlexibilityNo cancel feeOn-time63%

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