22 days in Chicago & San Juan Itinerary

22 days in Chicago & San Juan Itinerary

Created using Inspirock trip planner

Make it your trip
1
Chicago, United States
— 6 nights
Fly
2
San Juan, Puerto Rico
— 15 nights
Fly

S M T W T F S
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16

Chicago, United States

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, get a new perspective on nature at Field Museum, try to win big at Horseshoe Hammond, and get curious at Museum of Science and Industry.

For traveler tips, other places to visit, maps, and other tourist information, go to the Chicago online travel route planner.

If you are flying in from United States, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In December, daytime highs in Chicago are 38°F, while nighttime lows are 26°F. On the 27th (Sun), wrap the sightseeing up by early afternoon so you can travel to San Juan.

Things to do in Chicago

Museums · Parks · Childrens Museums · Historic Sites

Side Trips

Find places to stay Dec 21 — 27:

San Juan, Puerto Rico

— 15 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore the numerous day-trip ideas around San Juan: Zipline (in Rio Grande), El Yunque National Forest (El Portal Tropical Forest Center & El Yunque Rain Forest) and Ponce (Casa Wiechers-Villaronga, Museo de Arte de Ponce, &more). There's lots more to do: get to know the fascinating history of Old San Juan, trot along with a tour on horseback, walk around Parque Nacional de las Cavernas del Rio Camuy, and tour the pleasant surroundings at Condado Beach.

To find maps, photos, and tourist information, read our San Juan day trip planner.

Getting from Chicago to San Juan by flight takes about 8 hours. The time zone difference moving from Central Standard Time to Atlantic Standard Time is 2 hours. Traveling from Chicago in December, things will get much warmer in San Juan: highs are around 85°F and lows about 75°F. Finish your sightseeing early on the 11th (Mon) to allow enough time to travel back home.

Things to do in San Juan

Parks · Outdoors · Tours · Historic Sites

Side Trips

Find places to stay Dec 27 — Jan 11: