Sat 7 – Wed 11
Sunniest Places This Weekend from Chicago 2026
55 sunniest places with direct flights from Chicago this weekend. Guadalajara has the best conditions. Flights from €196 to Las Vegas.
Top Picks
Best Overall
Guadalajara
25°C
from €312
Sunniest
Guadalajara
from €312
Hottest
Abu Dhabi
29°C
from €1649
Cheapest Flight
Las Vegas
€196
Updated
Ranked by sunshine, temperature & flight price
Sunniest Places from Chicago
Last-minute pricing: flight prices this weekend can be higher and change quickly.
For more stable fares, see next weekend →
Max price
Sat 7 – Wed 11
Thu 5 – Sun 8
Fri 6 – Tue 10
Fri 6 – Mon 9
Sat 7 – Fri 13
Sat 7 – Wed 11
Sat 7 – Fri 13
Fri 6 – Thu 12
Thu 5 – Sun 8
Fri 6 – Mon 9
Fri 6 – Mon 9
Sat 7 – Tue 10
Sat 7 – Tue 10
Thu 5 – Sun 8
Fri 6 – Tue 10
Fri 6 – Tue 10
Sat 7 – Fri 13
Thu 5 – Tue 10
Thu 5 – Sun 8
Fri 6 – Mon 9
Fri 6 – Mon 9
Fri 6 – Mon 9
Fri 6 – Mon 9
Sat 7 – Thu 12
Frequently Asked Questions
Where is sunniest places this weekend from Chicago?
We found 55 sunniest places with direct flights from Chicago for this weekend. Guadalajara has the best conditions.
What is the cheapest sunniest place from Chicago?
Las Vegas is the cheapest option from Chicago, with return flights from €196.
How does HotWeekends pick Sunniest Places?
We combine live 14-day weather forecasts with real-time direct return flight prices for Saturday–Monday departures. A destination needs a Sky Condition Index of at least 6.0 out of 10 — roughly 'mostly sunny' — 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.