Noteworthy Tourist Destinations in Chicago:

Wrigley Field

Take the Red line to Addison. Arrive an hour or two before the game and walk around the outside the park. Waveland Ave and Sheffield Ave are fun at this time. Walk south on Clark from Wrigley for the bars. If you decide not to buy tickets, it’s fun to stick around after the crowds enter the park. My favorite bar in the area is Murphy’s Behind the Bleachers. It’s a great experience to watch the game in there and hear the crowd roar from directly across the street. Another option is to wait until the fifth or sixth inning and then pick up a ticket at a discount.

If you do make it to Wrigleyville you may want to spend a bit of time walking down a few side streets to get a feel for the surrounding neighborhood. Southport Ave, a few blocks west, is an area with boutique shops and restaurants that is worth a look.

Chicago Athletic Association

Located off Michigan Ave, across from Millennium Park. Amazing 19th century club atmosphere. Gorgeous game room in the back. Cherry Circle Room restaurant and bar feels like something out of the Guilded Age. Cindy’s rooftop bar looks out over Millennium Park and the Lake. If you visit, make sure to pass through the Drawing Room:


Located on North Ave Beach. Shaped like a giant ship. Upstairs is a super-casual open-air rooftop cafe with drinks and sandwiches. Great place to take in the Lakefront and watch a few dozen volleyball games being played.

The Lakefront Path runs directly past this place. You may decide to walk or bike (Divvy bike) to Castaways from a point further south along the Lakefront Path, such as Navy Pier, Grant Park, or the Museum Campus:

Divvy Bikes

Wicker Park

The hub of this neighborhood is the intersection of Milwaukee/ North/ Damen. Plenty of hipster trendster boutiques and eateries. This walking tour offers a look into the surrounding residential area:


Both of these places can have long wait times and it takes a while, like 40 min, to cook deep dish pizza.


Chicago Pizza and Oven Grinder:

Italian Beef:

When you order Italian beef, you will be asked if you want the entire sandwich dipped into the juice in which the beef simmers. I ask for the juice and on the side. I pour the juice onto the inside of the bun. People who take Italian beef seriously will condemn you for this, but whatever. I also ask for giardiniera peppers on the side. They are spicy. The milder alternative is sweet peppers. Also, these types of places almost always have delicious Italian and Polish sausage.

Mr. Beef — old school: