12 days in Chicago & Oakland Itinerary

12 days in Chicago & Oakland Itinerary

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Route & dates

12 days in Chicago & Oakland Itinerary

Start: Sao Paulo
Fly:  14​h 15​min
1
Chicago
— 4 nights
Fly:  6​h 45​min
2
Oakland
— 5 nights
Fly:  22​h
End: Sao Paulo


4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Bring the kids along to Bengtson's Pumpkin Farm and Museum of Science and Industry. Step out of Chicago with an excursion to Little Red Schoolhouse in Willow Springs--about 34 minutes away. There's much more to do: explore the world behind art at The Art Institute of Chicago, see the interesting displays at The Field Museum, take in panoramic vistas at Skydeck Chicago - Willis Tower, and meet the residents at Lincoln Park Zoo.

To find where to stay, traveler tips, maps, and more tourist information, go to the Chicago travel route planner .

Sao Paulo, Brazil to Chicago is an approximately 14.5-hour flight. The time zone difference moving from Brasilia Time (BRT) to Central Standard Time (CST) is minus 3 hours. Expect little chillier temperatures when traveling from Sao Paulo in October; daily highs in Chicago reach 21°C and lows reach 11°C. Cap off your sightseeing on the 19th (Fri) early enough to travel to Oakland.

Things to do in Chicago

Outdoors Parks Museums

Side Trips

Bengtson's Pumpkin Farm, Little Red Schoolhouse
Highlights from your plan
Bengtson's Pumpkin Farm ©
Bengtson's Pumpkin Farm
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium

5
nights
Oakland

Oakland ©
Oakland is the largest city and the county seat of Alameda County, California, United States. You'll visit kid-friendly attractions like Safari West and Armstrong Redwood State Reserve. Venture out of the city with trips to Fitzgerald J V Marine Reserve (in Moss Beach), Wine Tours & Tastings (in Napa) and Pride Mountain Vineyards (in St. Helena). The adventure continues: admire the majestic nature at Marin Headlands, explore and take pictures at Tilden Nature Area, explore the wealth of natural beauty at Muir Woods National Monument, and stop by Petaluma Seed Bank.

To find out how to plan a trip to Oakland, use our trip itinerary maker.

Getting from Chicago to Oakland by flight takes about 7 hours. Other options: do a combination of flight and subway; or drive. You'll gain 2 hours traveling from Chicago to Oakland due to the time zone difference. While traveling from Chicago, expect somewhat warmer days and about the same nights in Oakland, ranging from highs of 26°C to lows of 13°C. Cap off your sightseeing on the 24th (Wed) early enough to travel back home.

Things to do in Oakland

Parks Wildlife Nature

Side Trips

Muir Woods National Monument, Pride Mountain Vineyards, Petaluma Seed Bank, Fitzgerald J V Marine Reserve, Safari West
Highlights from your plan
Tilden Nature Area ©
Tilden Nature Area
Muir Woods National Monument ©
Muir Woods National Monument
Wine Tours & Tastings

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