$103 Find Cheap Flights from Chicago to Delray Beach - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Delray Beach departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$225
Typical prices: $330-$517
Frontier
Tue 7/14Tue 7/14
MDW - MIA • 1 stop
Cheapest non-stop
$237
Typical prices: $292-$502
Southwest
Wed 9/23Mon 9/28
MDW - MIA • Non-stop
Arrival airport
You can't fly directly to Delray Beach. It is served by Miami (MIA), located 47.8 miles from Delray Beach.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Delray Beach (CHI-MIA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Delray Beach that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Delray Beach

Tue, Jul 14 - Tue, Jul 14
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
Frontier Logo
5:28 pm - 10:03 pm
MIA
-
MDW
5h 35m
1 stop
$225Frontier
Sat, Aug 1 - Tue, Aug 4
United Airlines Logo
6:05 pm - 10:27 pm
ORD
-
MIA
3h 22mnonstop
United Airlines Logo
8:48 am - 2:53 pm
MIA
-
ORD
7h 05m
1 stop
$225United Airlines
Sat, Oct 24 - Tue, Oct 27
Frontier Logo
6:40 am - 6:22 pm
MDW
-
MIA
10h 42m
1 stop
Frontier Logo
6:45 am - 10:58 am
MIA
-
MDW
5h 13m
1 stop
$226Frontier
Thu, Aug 6 - Wed, Aug 12
Frontier Logo
11:06 am - 5:47 pm
MDW
-
MIA
5h 41m
1 stop
Frontier Logo
10:50 am - 10:03 pm
MIA
-
MDW
12h 13m
1 stop
$227Frontier
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
5:30 am - 2:40 pm
MDW
-
MIA
8h 10m
1 stop
Southwest Logo
7:00 am - 2:10 pm
MIA
-
MDW
8h 10m
2 stops
$228Southwest
Wed, Jul 15 - Tue, Jul 21
Frontier Logo
9:57 pm - 5:51 am
ORD
-
MIA
30h 54m
1 stop
Frontier Logo
10:15 pm - 5:37 am
MIA
-
ORD
32h 22m
1 stop
$228Frontier
Wed, Jul 15 - Wed, Jul 22
Frontier Logo
6:05 am - 1:53 pm
MDW
-
MIA
6h 48m
1 stop
Frontier Logo
5:28 pm - 10:03 pm
MIA
-
MDW
5h 35m
1 stop
$229Frontier
Sat, Aug 8 - Wed, Aug 12
Southwest Logo
6:45 am - 1:35 pm
MDW
-
MIA
5h 50m
1 stop
Southwest Logo
4:00 pm - 6:05 pm
MIA
-
MDW
3h 05mnonstop
$231Southwest
Tue, Jul 14 - Wed, Jul 22
United Airlines Logo
6:00 am - 4:16 pm
ORD
-
MIA
9h 16m
1 stop
United Airlines Logo
12:30 pm - 3:13 pm
MIA
-
ORD
3h 43mnonstop
$231United Airlines
Sat, Dec 12 - Mon, Dec 14
American Airlines Logo
7:07 pm - 11:25 pm
ORD
-
MIA
3h 18mnonstop
American Airlines Logo
8:35 pm - 10:57 pm
MIA
-
ORD
3h 22mnonstop
$237American Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$103
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago O'Hare Airport to Miami

When to book flights from Chicago to Delray Beach

Are your dates flexible? Find out the best times to travel from Chicago to Delray Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Delray Beach

  • Which airports will I be using when flying from Chicago to Delray Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Delray Beach does not have its own airport so you’ll be flying into nearby Miami airport, which is 47.8 mi away.

  • How long does a flight from Chicago to Delray Beach take?

    Direct flights cover the 1,186 miles separating Chicago and Delray Beach in about 3h 00m.

  • How many flights are there between Chicago and Delray Beach?

    52 direct flights run between Chicago and Delray Beach on a daily basis. On average, there are about 367 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Delray Beach?

    Consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Delray Beach?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Delray Beach.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Delray Beach?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Delray Beach from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Delray Beach?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Delray Beach with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Delray Beach?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Delray Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Delray Beach?

    In the last 5 days, the cheapest one-way ticket between Chicago and Delray Beach found on KAYAK was with Frontier for $32. Frontier offered a round-trip connection from $57 and JetBlue from $89.

Top tips for finding cheap flights from Chicago to Delray Beach

  • There is no airport in Delray Beach. Instead, you’ll be flying into Miami Airport when flying between Chicago and Delray Beach.
  • The cheapest flight from Chicago to Delray Beach was found 76 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Delray Beach

 
Need help choosing which airline to fly with from Chicago to Delray Beach? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4245 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Always wish for more healthy, gluten free options. We have to bring our own.

Our seats were all the way in back of the plane,

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Chicago to Delray Beach

Complete your trip to Delray Beach with a hotel stay or car rental