Art Institute of Chicago, James Beard Award-Winning Eats, Kickass Comedy

You have a long day's drive ahead of you across Ohio and Indiana so check out early and hit the road, arriving at the Mocha House in Warren, Ohio for strong coffee and breakfast. Hop back in the car and keep moving.

Arrive in the Windy City just before 2pm, then check into your stylish digs at the Pendry, a boutique hotel in the 1929 art deco Carbide & Carbon Building just a 5-minute walk from the Chicago River.

Stroll over to the Art Institute of Chicago and browse the galleries for an hour. Afterwards, just walk the streets of this gorgeous city for a while, heading in the direction of the West Loop, an emerging neighborhood where scores of excellent eateries have moved into historic warehouses, turning the area into a foodie heaven.
The Art Institute is closed on Tuesdays and Wednesdays.

Stop off at Millenium Park with its three blocks of open lakefront, ferris wheel, sculptures, and skating rink. A favorite spot for people watching, the park is one of the most popular spots in downtown Chicago.

Arrive at the restaurant by about 5pm and make sure you make a reservation in advance. This is one of the hottest dinner tickets in Chicago, and you'll see why once you start eating. Enjoy the culinary experience of James Beard Award-winning chef Stephanie Izard. And ask your server if they still have the divine escargot tortellini on the menu!
Open for dinner daily.

Get tickets for Second City, a comedy venue that has historically been a breeding ground for many Saturday Night Live comedians! Take in at 8pm show and laugh until you just can't anymore.
Book tickets in advance.

End your night at one of Chicago's swankiest bars, the James Beard Award-winning Aviary. The bar, with its creative concoctions and vintage interiors, feels like a swanky speakeasy and is a great way to end your first night in the Windy City.
Closed Monday and Tuesday.

Goodnight to all that and more! Sweet dreams as you hit the pillow in your posh, downtown hotel.