Navy Pier - Near North Side - Chicago, IL

Boka - Lincoln Park - Chicago, IL

Garrett Popcorn Shops - Near North Side - Chicago, IL

Grant Park - The Loop - Chicago, IL

Willis Tower - The Loop - Chicago, IL

formerly sears tower

The Bongo Room - South Loop - Chicago, IL

breakfast/brunch

Violet Hour - Wicker Park - Chicago, IL

lounge

Gilt Bar - Near North Side - Chicago, IL

cheap-ish pastas

Mana Food Bar - Wicker Park - Chicago, IL

vegetarian

Longman & Eagle - Logan Square - Chicago, IL

Hot Doug's - Avondale - Chicago, IL

Girl & The Goat - Near West Side - Chicago, IL

Millennium Park - The Loop - Chicago, IL

Alinea - Lincoln Park - Chicago, IL

Gott's Roadside - Napa, CA

Gott's Roadside - St. Helena, CA

Bouchon Bakery - Yountville, CA

Domaine Carneros - Napa, CA

V. Sattui Winery - Saint Helena, CA

Grgich Hills Estate - Rutherford, CA

Gotts's Roadside

Lula Café - Logan Square - Chicago, IL

good breakfast/brunch

Millennium Park - The Loop - Chicago, IL

the bean!

Grant Park - The Loop - Chicago, IL

the fountain!

Sears Tower - The Loop - Chicago, IL

must see! but skydeck...expensive and long wait

The Magnificent Mile - GNMAA

SHOPPING

Bongo Room - South Loop - Chicago, IL

brunch on weekends only

Navy Pier - Near North Side - Chicago, IL

very touristy, a bunch of shops, view of lake michigan but a lot of people say it's overrated. fireworks

Violet Hour - Wicker Park - Chicago, IL

good drinks

Hot Doug's

Longman & eagle Chicago

Gilt Bar - Near North Side - Chicago, IL

Girl & the Goat - Near West Side - Chicago, IL

Alinea - Lincoln Park - Chicago, IL

Mana Food Bar - Wicker Park - Chicago, IL