5 days in Chicago & San Diego Itinerary

5 days in Chicago & San Diego Itinerary

Created using Inspirock United States journey planner

Make it your trip
1
Chicago
— 2 nights
Fly
2
San Diego
— 2 nights
Fly

S M T W T F S
29
30
31
1
2
3
4

Chicago

— 2 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Discover out-of-the-way places like Chicago Botanic Garden and Morton Arboretum. Next up on the itinerary: test your team's savvy at The Escape Game Chicago, don't miss a visit to Skydeck Chicago - Willis Tower, ponder the design of Buckingham Fountain, and admire the natural beauty at Garfield Park Conservatory.

To find photos, more things to do, traveler tips, and tourist information, read our Chicago trip builder tool.

The Route module shows you travel options from your home to Chicago. In December, daytime highs in Chicago are 38°F, while nighttime lows are 26°F. Cap off your sightseeing on the 31st (Tue) early enough to travel to San Diego.

Things to do in Chicago

Parks · Museums · Breweries & Distilleries · Tours

Side Trips

Find places to stay Dec 29 — 31:

San Diego

— 2 nights

America's Finest City

Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Kick off your visit on the 1st (Wed): look for all kinds of wild species at Lions, Tigers & Bears, appreciate the history behind Mt. Soledad National Veterans Memorial, and then explore the different monuments and memorials at Fort Rosecrans Cemetery. Here are some ideas for day two: examine the collection at USS Midway Museum and then appreciate the history behind The Unconditional Surrender.

To find other places to visit, ratings, where to stay, and other tourist information, read San Diego trip itinerary planner.

Getting from Chicago to San Diego by flight takes about 6.5 hours. Other options: drive; or take a bus. Due to the time zone difference, you'll gain 2 hours traveling from Chicago to San Diego. Plan for much warmer temperatures traveling from Chicago in December, with highs in San Diego at 68°F and lows at 51°F. On the 2nd (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in San Diego

Historic Sites · Museums · Wildlife · Parks

Side Trip

Find places to stay Dec 31 — Jan 2: