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$45+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Find cheap flights from Chicago to Delray Beach with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Delray Beach are usually found in September or January, booked 69 days in advance, depart on a Monday or Thursday and return on a Friday

Cheap 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 December 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/23. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/72:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 12/23$102
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 1/711:43 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 12/21$108
This WAYA deal was found by Cheapflights users on 12/23. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Wed 1/75:07 pmMIA - ORD
1 stop6h 32mMultiple Airlines
Deal found 12/23$110
This Kiwi.com deal was found by Cheapflights users on 12/23. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Tue 1/67:09 pmMIA - ORD
1 stop28h 30mMultiple Airlines
Deal found 12/23$116
This Mytrip deal was found by Cheapflights users on 12/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/217:00 amMIA - ORD
2 stops15h 03mSpirit Airlines
Deal found 12/22$123
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Tue 1/612:49 pmMIA - MDW
1 stop10h 28mFrontier
Deal found 12/21$129
This Mytrip deal was found by Cheapflights users on 12/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Thu 2/57:00 amMIA - ORD
2 stops15h 03mSpirit Airlines
Deal found 12/21$136
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Fri 1/93:48 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 12/21$146
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mMultiple Airlines
Mon 1/59:59 pmMIA - MDW
1 stop25h 18mMultiple Airlines
Deal found 12/21$148
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Fri 1/94:04 pmMIA - MDW
1 stop7h 17mFrontier
Deal found 12/21$167
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Tue 12/306:50 amORD - MIA
1 stop14h 09mMultiple Airlines
Sat 1/105:54 amMIA - ORD
Nonstop3h 24mMultiple Airlines
Deal found 12/22$169
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Thu 1/83:48 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 12/21$173

Find 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 December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$93
(Kiwi.com)

One-way from

$45
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$352
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
Search Deals
From Chicago (CHI) to Delray Beach
Search Deals
One-way flight from Chicago (CHI) to Delray Beach
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 23, 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

MDW - MIA

MDWMIA

Chicago Midway

Mon 1/26

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 1/31

6:30 am-8:40 am

Nonstop3h 10m

$168

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 2/4

7:05 am-3:27 pm

1 stop7h 22m

Miami

Fri 2/6

1:21 pm-6:49 pm

1 stop6h 28m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 1/28

1:58 pm-10:03 pm

1 stop7h 05m

Miami

Thu 2/5

8:15 am-1:40 pm

1 stop6h 25m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 2/1

1:58 pm-10:03 pm

1 stop7h 05m

Miami

Fri 2/6

10:29 am-4:55 pm

1 stop7h 26m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/20

10:48 am-6:20 pm

1 stop6h 32m

Miami

Tue 1/27

8:05 am-12:49 pm

1 stop5h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/20

10:48 am-6:20 pm

1 stop6h 32m

Miami

Wed 1/21

7:15 am-11:59 am

1 stop5h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/15

4:13 pm-12:53 am

1 stop7h 40m

Miami

Fri 2/20

7:15 am-11:59 am

1 stop5h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/10

10:48 am-5:15 pm

1 stop5h 27m

Miami

Thu 2/19

12:00 pm-5:45 pm

1 stop6h 45m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 2/5

7:30 am-11:55 am

Nonstop3h 25m

Miami

Tue 2/10

4:19 pm-6:55 pm

Nonstop3h 36m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/27

7:30 am-11:55 am

Nonstop3h 25m

Miami

Tue 1/27

4:19 pm-6:55 pm

Nonstop3h 36m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 43 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 December 19, 2025.

The best time to book flights from Chicago to Delray Beach is 69 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, October is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $45). Flying from Chicago to Delray Beach in June is currently the most expensive (average of $117). 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 December 23, 2025.

When flying from Chicago to Delray Beach, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 13% versus a flight in the afternoon.

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 Wednesday at noon when fares are most often at their lowest. Friday at noon 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 December 23, 2025.

The most flights from CHI to DB9 are scheduled on a Saturday (56 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (22 on average).

How much does it cost to fly round-trip from Chicago to Delray Beach?

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 December 23, 2025.
Read through reviews of airlines operating flights from Chicago to Delray Beach, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

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.
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

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
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

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
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

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
5.8
Fair
3,075 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

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 Delray Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Delray Beach?

    Southwest, Delta, and United Airlines can get you from Chicago to Delray Beach in just under 3h. Your travel time can differ by up to 4h 22m. Airlines will cover a distance of 1183 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Delray Beach one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $39. Users have also found prices from $42 and $78 on Spirit Airlines and Southwest, 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 ANA (100%), Emirates (88%) or Spirit Airlines (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 $528, our data indicates the cheapest price to be $53. The most popular route (Chicago O'Hare Intl - Miami), is priced around $51.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $45). Flying from Chicago to Delray Beach in June is currently the most expensive (average of $117). 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 9 airlines flying from Chicago to Delray Beach

Discover the top 9 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$174FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$186FlexibilityNo cancel feeOn-time65%
DeltaCheapest$125Average$359FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$127Average$365FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$130Average$302FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$138Average$222FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$153Average$323FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$166Average$387FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%

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