HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Delray Beach

$55+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Delray Beach with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Delray Beach are usually found in September or January, booked 41 days in advance, depart on a Monday or Thursday and return on a Friday

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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/62:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sat 12/139:38 amMIA - MDW
1 stop12h 44mFrontier
Deal found 10/26$105
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 12/67:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Thu 12/114:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 10/26$105
This Frontier deal was found by Cheapflights users on 10/26. 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 11/206:05 amMDW - MIA
1 stop10h 04mFrontier
Wed 11/262:44 pmMIA - MDW
Nonstop3h 13mFrontier
Deal found 10/26$106
This Priceline deal was found by Cheapflights users on 10/27. 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.
Sat 12/67:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sat 12/134:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 10/27$106
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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.
Thu 12/117:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sun 12/144:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 10/26$107
This WAYA deal was found by Cheapflights users on 10/28. 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.
Thu 12/112:16 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 12/245:30 amMIA - MDW
1 stop8h 51mFrontier
Deal found 10/28$108
This Priceline deal was found by Cheapflights users on 10/27. 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 12/117:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 12/242:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 10/27$108
This CheapOair deal was found by Cheapflights users on 10/26. 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.
Sat 11/82:05 pmMDW - MIA
Nonstop3h 00mFrontier
Sat 11/152:20 pmMIA - MDW
1 stop21h 06mFrontier
Deal found 10/26$109
This Frontier deal was found by Cheapflights users on 10/26. 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.
Mon 11/101:37 pmMDW - MIA
1 stop9h 57mFrontier
Thu 11/1311:31 amMIA - MDW
1 stop10h 00mFrontier
Deal found 10/26$110
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/2011:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Mon 11/248:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 10/28$112
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/236:14 amMDW - MIA
1 stop12h 16mFrontier
Sat 12/276:59 amMIA - MDW
Nonstop3h 20mFrontier
Deal found 10/27$113
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/2511:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Thu 12/44:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 10/28$113

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 October 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$105
(Kiwi.com)

One-way from

$55
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$267
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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 28, 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

Tue 1/13

6:00 am-1:35 pm

1 stop6h 35m

Miami

Tue 1/13

2:35 pm-4:50 pm

Nonstop3h 15m

$167

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 12/6

1:15 pm-8:45 pm

1 stop6h 30m

Miami

Wed 12/10

1:05 pm-3:20 pm

Nonstop3h 15m

$187

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 1/12

9:34 am-5:48 pm

1 stop7h 14m

Miami

Sat 1/24

8:05 am-12:48 pm

1 stop5h 43m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 1/7

9:34 am-5:48 pm

1 stop7h 14m

Miami

Sat 1/10

8:05 am-12:48 pm

1 stop5h 43m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/27

5:33 am-12:14 pm

1 stop5h 41m

Miami

Sat 2/7

6:00 am-10:15 am

1 stop5h 15m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 1/31

5:59 pm-12:51 am

1 stop5h 52m

Miami

Tue 2/10

6:00 am-10:08 am

1 stop5h 08m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 2/3

10:35 am-5:48 pm

1 stop6h 13m

Miami

Wed 2/4

6:00 am-10:08 am

1 stop5h 08m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 12/2

10:49 am-5:25 pm

1 stop5h 36m

Miami

Wed 12/3

8:10 am-12:34 pm

1 stop5h 24m

$218

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/13

6:10 am-12:00 pm

1 stop4h 50m

Miami

Tue 1/20

2:35 pm-4:50 pm

Nonstop3h 15m

$238

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 11/17

9:51 am-5:18 pm

1 stop6h 27m

Miami

Wed 11/19

8:05 am-12:19 pm

1 stop5h 14m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 45 results
1
2
3
...
5

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 October 24, 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, February is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $47). 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 October 28, 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 12% 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. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 28, 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
4,240 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
8,116 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
3,124 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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 and Delta can get you from Chicago to Delray Beach in just under 6h 35m. Your travel time can differ by up to 39m. Airlines will cover a distance of 1183 mi. This flight may include one or multiple stops.

  • 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 Spirit Airlines (88%), United Airlines (86%) or Alaska Airlines (82%) 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 $655, our data indicates the cheapest price to be $59. The most popular route (Chicago O'Hare Intl - Miami), is priced around $84.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Delray Beach (average of $47). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Delray Beach

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
Midway to Miami flights
O'Hare Intl to Sarasota flights
Midway to Fort Lauderdale flights
O'Hare Intl to West Palm Beach flights
St. Louis to Orlando flights
Midway to Tampa flights
O'Hare Intl to Key West flights
Midway to Fort Myers flights
O'Hare Intl to Jacksonville flights
St. Louis to Miami flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
St. Louis to Tampa flights
St. Louis to Fort Lauderdale flights
St. Louis to Key West flights
O'Hare Intl to Panama City flights
Rockford to St Petersburg flights
Midway to Key West flights
Moline to Orlando flights
Midway to Jacksonville flights
Rockford to Orlando Sanford Intl flights
Midway to Sarasota flights
St. Louis to Sarasota flights
St. Louis to Fort Myers flights
Midway to Pensacola flights
Peoria to Orlando flights
Moline to Tampa flights
O'Hare Intl to Valparaiso flights
Moline to Fort Lauderdale flights
Peoria to Miami flights
O'Hare Intl to Daytona Beach flights
Springfield to Orlando flights
Peoria to Fort Lauderdale flights
Rockford to Punta Gorda flights
Midway to Panama City flights
St. Louis to Jacksonville flights
Moline to Fort Myers flights
Moline to Sarasota flights
Moline to St Petersburg flights
Evansville to Orlando flights
St. Louis to Pensacola flights
Peoria to Fort Myers flights
St. Louis to West Palm Beach flights
Peoria to Punta Gorda flights

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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$190FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$213FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$363FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$153Average$323FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$422FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$354FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.