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$65+ 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
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$125
(Booking.com)

One-way from

$65
(eDestinos)

Popular in

December

Cheapest in

July

Average price

$272
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. 14% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This Booking.com deal was found by Cheapflights users on 4/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/75:51 amORD - MIA
1 stop6h 15mSpirit Airlines
Sat 5/103:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 4/21$125
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Tue 5/209:55 amORD - MIA
Nonstop3h 15mMultiple Airlines
Sat 5/246:00 amMIA - ORD
1 stop18h 52mMultiple Airlines
Deal found 4/21$143
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/205:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Wed 5/217:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 4/21$177
This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/125:21 pmORD - MIA
1 stop11h 01mFrontier
Sun 5/187:12 amMIA - ORD
1 stop9h 45mFrontier
Deal found 4/21$198
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:57 amORD - MIA
Nonstop3h 08mAmerican Airlines
Sun 9/78:01 pmMIA - ORD
Nonstop3h 33mAmerican Airlines
Deal found 4/22$210
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:15 pmORD - MIA
1 stop5h 31mDelta
Sat 5/318:40 amMIA - ORD
1 stop5h 01mDelta
Deal found 4/21$217
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/410:25 amMDW - MIA
1 stop7h 00mDelta
Sat 6/75:35 amMIA - MDW
1 stop5h 05mDelta
Deal found 4/22$217
This JetBlue deal was found by Cheapflights users on 4/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/154:03 pmORD - MIA
1 stop7h 10mJetBlue
Sat 5/177:00 amMIA - ORD
1 stop9h 04mJetBlue
Deal found 4/20$265
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Tue 5/207:30 amORD - MIA
Nonstop3h 18mUnited Airlines
Wed 5/284:17 pmMIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 4/20$267
This Kissandfly.com deal was found by Cheapflights users on 4/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:30 amMDW - MIA
1 stop13h 05mFrontier
Thu 6/128:11 amMIA - MDW
1 stop5h 18mFrontier
Deal found 4/21$279

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 April 22, 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

Wed 5/7

5:51 am-1:06 pm

1 stop6h 15m

Miami

Sat 5/10

3:15 pm-5:41 pm

Nonstop3h 26m

$125

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 5/20

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Sat 5/24

6:00 am-11:52 pm

1 stop18h 52m

$143

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 5/20

5:10 pm-9:05 pm

Nonstop2h 55m

Miami

Wed 5/21

7:00 am-9:10 am

Nonstop3h 10m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/22

2:58 pm-11:43 pm

1 stop7h 45m

Miami

Wed 5/28

9:30 am-2:22 pm

1 stop5h 52m

$188

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/24

7:16 pm-11:32 pm

Nonstop3h 16m

Miami

Thu 5/29

1:40 pm-4:05 pm

Nonstop3h 25m

$210

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/24

5:15 pm-11:46 pm

1 stop5h 31m

Miami

Tue 5/27

7:30 pm-11:58 pm

1 stop5h 28m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 6/4

9:16 am-6:07 pm

1 stop7h 51m

Miami

Tue 6/10

5:30 am-9:41 am

1 stop5h 11m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/15

4:03 pm-12:13 am

1 stop7h 10m

Miami

Sat 5/17

7:00 am-3:04 pm

1 stop9h 04m

$265

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 5/20

7:30 am-11:48 am

Nonstop3h 18m

Miami

Wed 5/28

4:17 pm-6:51 pm

Nonstop3h 34m

$267

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 6/5

6:30 am-8:35 pm

1 stop13h 05m

Miami

Thu 6/12

8:11 am-12:29 pm

1 stop5h 18m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

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 18, 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 $229). 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 April 22, 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 April 22, 2025.

The most flights from CHI to DB9 are scheduled on a Monday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 April 22, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Avelo Airlines 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.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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.
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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
8,683 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

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.

  • 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 $65. Users have also found prices from $89 and $90 on American 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 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 $974, our data indicates the cheapest price to be $57. The most popular route (Chicago O'Hare Intl - Miami), is priced around $88.

  • 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 $229). 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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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$42Average$179FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$160Average$352FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$177Average$354FlexibilityNo cancel feeOn-time69%
DeltaCheapest$177Average$374FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$201Average$398FlexibilityNo cancel feeOn-time63%

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