Chicago to Delray Beach Flights (CHI-PBI) from $21

Choose two or more items and save on your trip:

Wander Wisely with exceptional service, 24/7 support

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Selected fares from Chicago to Delray Beach

The cheapest prices found with in the last 7 days for return flights were $41 and $21 for one-way flights to Delray Beach for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, May 28 - Wed, May 29
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$41 Roundtrip, found 1 hour ago
$41
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, May 28 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, May 29, priced at $41 found 1 hour ago
Frontier Airlines
Sat, Jun 1 - Wed, Jun 12
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$110 Roundtrip, found 15 hours ago
$110
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Jun 1 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Jun 12, priced at $110 found 15 hours ago
Frontier Airlines
Wed, Aug 21 - Sat, Aug 24
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$110 Roundtrip, found 18 hours ago
$110
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Wed, Aug 21 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Aug 24, priced at $110 found 18 hours ago

Save more with Delray Beach Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
per person
Jul 4 - Jul 9
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
per person
Jun 24 - Jun 29
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Kimpton EPIC Hotel, an IHG Hotel

Kimpton EPIC Hotel, an IHG Hotel

5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 18
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 18
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Don't see what you're looking for?
See all available trips from Chicago to Delray Beach
View all trips