5 days in Chicago & San Diego Itinerary

5 days in Chicago & San Diego Itinerary

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Route & dates

5 days in Chicago & San Diego Itinerary

Start: Chicago
1
Chicago
— 2 nights
Fly:  6​h 15​min
2
San Diego
— 2 nights
Fly:  6​h 15​min
End: Chicago

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Lake Michigan and The Escape Game Chicago. Explore the numerous day-trip ideas around Chicago: Morton Arboretum (in Lisle) and Chicago Botanic Garden (in Glencoe). There's lots more to do: explore the world behind art at The Art Institute of Chicago, examine the collection at Richard H. Driehaus Museum, take in panoramic vistas at Skydeck Chicago - Willis Tower, and walk around Millennium Park.

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

The Route module shows you travel options from your home to Chicago. In December, daily temperatures in Chicago can reach 38°F, while at night they dip to 26°F. Wrap up your sightseeing on the 31st (Tue) to allow time to travel to San Diego.

Things to do in Chicago

Parks Museums Tours

Side Trips

Morton Arboretum, Lake Michigan, Chicago Botanic Garden
Find places to stay Dec 29 — 31:
Highlights from your plan
The Escape Game Chicago ©
The Escape Game Chicago
Lake Michigan ©
Lake Michigan
The Art Institute of Chicago ©
The Art Institute of Chicago

2
nights
San Diego

San Diego ©
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.
Start off your visit on the 1st (Wed): identify plant and animal life at Lions, Tigers & Bears, then pause for some photo ops at Mt. Soledad National Veterans Memorial, and then stroll the grounds of Fort Rosecrans Cemetery. Get ready for a full day of sightseeing on the 2nd (Thu): see the interesting displays at USS Midway Museum and then appreciate the history behind The Unconditional Surrender.

For where to stay, reviews, ratings, and other tourist information, read our San Diego trip planner.

Getting from Chicago to San Diego by flight takes about 6.5 hours. Other options: drive; or take a train. Due to the time zone difference, you'll gain 2 hours traveling from Chicago to San Diego. Traveling from Chicago in December, things will get much warmer in San Diego: highs are around 68°F and lows about 51°F. Wrap up your sightseeing by early afternoon on the 2nd (Thu) to allow enough time to travel back home.

Things to do in San Diego

Historic Sites Museums Parks

Side Trip

Lions, Tigers & Bears
Find places to stay Dec 31 — Jan 2:
Highlights from your plan
Lions, Tigers & Bears ©
Lions, Tigers & Bears
Fort Rosecrans Cemetery ©
Fort Rosecrans Cemetery
USS Midway Museum ©
USS Midway Museum

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