See & Do

Buckingham Fountain

Sam visits one of the largest fountains in the world.

500 South Shore Dr., Chicago, IL 60605

Eat

The Map Room

This travelers tavern represents 36 different brewing styles from all over the world with 200 unique brands of beer.

1949 North Hoyne, Chicago, IL 60647

Eat

Moto Restaurant

Molecular gastronomy meets hip meat-packing district.

945 West Fulton Market, Chicago, IL 60607

Sleep

The James Hotel

Sam unwinds in one of Chicago's most stylish and luxurious hotels.

55 East Ontario, Chicago, IL 60611

See & Do

Daley Center

Critical Mass of 2,000 cyclists raise eco awareness all year long and cycle around the city.

50 West Washington, Chicago, IL 60602

See & Do

Millennium Park

Sam strolls through this 24.5-acre park with a 3-story Bean.

201 East Randolph St., Chicago, IL 60601

See & Do

Second City

Sam makes a stop at this legendary improv comedy theatre.

1616 North Wells, Chicago, IL 60614

See & Do

Buddy Guy's Legends

Sam's in the mood to hear some blues!

754 South Wabash, Chicago, IL 60605

See & Do

Wrigley Field Rooftop Club

Sam roots for Chicago baseball on the rooftop bar.

3617 North Sheffield, Chicago, IL 60613

See & Do

Suffolk Downs

Horse-racing kicks up the pace for the weekend.