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Warmest Destinations Next Weekend from Chicago 2026

20 warmest destinations with direct flights from Chicago next weekend. Abu Dhabi has the best conditions. Flights from €106 to Memphis.

Top Picks

Guadalajara
Best Overall Guadalajara 24°C from €342
San Juan
Sunniest San Juan Clear skies from €394
Abu Dhabi
Hottest Abu Dhabi 29°C from €1649
Memphis
Cheapest Flight Memphis €106 Clear skies
Search all destinations from Chicago →
Updated Ranked by sunshine, temperature & flight price

Warmest Destinations from Chicago

14-day forecast: weather for next weekend gives a good indication of conditions, but accuracy improves as the weekend gets closer. See this weekend →
Max price
Abu Dhabi, United Arab Emirates Sat 14 – Thu 19
#1

Abu Dhabi, United Arab Emirates

29°C Mostly sunny from €1649

Sat 14 – Thu 19 Nov · 5 nights

Sat 27°C
Sun 27°C
Mon 27°C
Tue 27°C
Wed 27°C
San Juan, United States Sat 14 – Tue 17
#2

San Juan, United States

28°C Clear skies from €394

Sat 14 – Tue 17 Nov · 3 nights

Sat 22°C
Sun 22°C
Mon 24°C
Tue 24°C
Montego Bay, Jamaica Thu 12 – Sun 15
#3

Montego Bay, Jamaica

27°C Clear skies from €391

Thu 12 – Sun 15 Nov · 3 nights

Thu 27°C
Fri 28°C
Sat 29°C
Sun 27°C
San Jose del Cabo, Mexico Thu 12 – Sun 15
#4

San Jose del Cabo, Mexico

26°C Clear skies from €604

Thu 12 – Sun 15 Nov · 3 nights

Thu 27°C
Fri 26°C
Sat 27°C
Sun 26°C
Austin, United States Sat 14 – Tue 17
#5

Austin, United States

25°C Clear skies from €236

Sat 14 – Tue 17 Nov · 3 nights

Sat 22°C
Sun 20°C
Mon 24°C
Tue 25°C
San Antonio, United States Sat 14 – Wed 18
#6

San Antonio, United States

25°C Clear skies from €234

Sat 14 – Wed 18 Nov · 4 nights

Sat 22°C
Sun 22°C
Mon 25°C
Tue 25°C
Wed 25°C
Dallas, United States Sat 14 – Wed 18
#7

Dallas, United States

25°C Mostly sunny from €148

Sat 14 – Wed 18 Nov · 4 nights

Sat 22°C
Sun 20°C
Mon 23°C
Tue 20°C
Wed 26°C
Guadalajara, Mexico Fri 13 – Tue 17
#8

Guadalajara, Mexico

24°C Clear skies from €342

Fri 13 – Tue 17 Nov · 4 nights

Fri 25°C
Sat 26°C
Sun 27°C
Mon 27°C
Tue 26°C
Fort Lauderdale, United States Thu 12 – Sun 15
#9

Fort Lauderdale, United States

24°C Clear skies from €442

Thu 12 – Sun 15 Nov · 3 nights

Thu 26°C
Fri 26°C
Sat 24°C
Sun 25°C
Miami, United States Thu 12 – Sun 15
#10

Miami, United States

23°C Clear skies from €379

Thu 12 – Sun 15 Nov · 3 nights

Thu 25°C
Fri 26°C
Sat 24°C
Sun 25°C
Orlando, United States Thu 12 – Sun 15
#11

Orlando, United States

22°C Clear skies from €377

Thu 12 – Sun 15 Nov · 3 nights

Thu 24°C
Fri 25°C
Sat 25°C
Sun 26°C
Jacksonville, United States Thu 12 – Sun 15
#12

Jacksonville, United States

22°C Clear skies from €452

Thu 12 – Sun 15 Nov · 3 nights

Thu 25°C
Fri 22°C
Sat 23°C
Sun 24°C
Savannah, United States Thu 12 – Mon 16
#13

Savannah, United States

21°C Clear skies from €474

Thu 12 – Mon 16 Nov · 4 nights

Thu 21°C
Fri 18°C
Sat 20°C
Sun 22°C
Mon 23°C
Phoenix, United States Thu 12 – Sun 15
#14

Phoenix, United States

20°C Mostly sunny from €266

Thu 12 – Sun 15 Nov · 3 nights

Thu 25°C
Fri 25°C
Sat 22°C
Sun 21°C
Amman, Jordan Fri 13 – Mon 16
#15

Amman, Jordan

20°C Mostly sunny from €1368

Fri 13 – Mon 16 Nov · 3 nights

Fri 20°C
Sat 22°C
Sun 19°C
Mon 16°C
Charleston, United States Fri 13 – Mon 16
#16

Charleston, United States

20°C Clear skies from €294

Fri 13 – Mon 16 Nov · 3 nights

Fri 16°C
Sat 18°C
Sun 20°C
Mon 22°C
Santa Ana, United States Thu 12 – Sun 15
#17

Santa Ana, United States

19°C Mostly sunny from €522

Thu 12 – Sun 15 Nov · 3 nights

Thu 23°C
Fri 22°C
Sat 23°C
Sun 21°C
Palm Springs, United States Thu 12 – Sun 15
#18

Palm Springs, United States

19°C Mostly sunny from €543

Thu 12 – Sun 15 Nov · 3 nights

Thu 24°C
Fri 24°C
Sat 22°C
Sun 20°C
Memphis, United States Sat 14 – Tue 17
#19

Memphis, United States

19°C Clear skies from €106

Sat 14 – Tue 17 Nov · 3 nights

Sat 20°C
Sun 21°C
Mon 19°C
Tue 22°C
Birmingham, United States Sat 14 – Wed 18
#20

Birmingham, United States

18°C Mostly sunny from €242

Sat 14 – Wed 18 Nov · 4 nights

Sat 19°C
Sun 21°C
Mon 22°C
Tue 21°C
Wed 19°C

Frequently Asked Questions

Where is warmest destinations next weekend from Chicago?

We found 20 warmest destinations with direct flights from Chicago for next weekend. Abu Dhabi has the best conditions.

What is the cheapest warmest destination from Chicago?

Memphis is the cheapest option from Chicago, with return flights from €106.

How does HotWeekends pick Warmest Destinations?

We combine live 14-day weather forecasts with real-time direct return flight prices for Saturday–Monday departures. A destination needs an average daytime temperature of at least 18°C to appear on this page.

Can I filter by budget or number of nights?

Yes. Use the full search from Chicago to filter by max flight price, hotel budget, number of nights, and more.