Chicago

Getting There

From Ohare Airport

The blue line will take you into the city. At the O'Hare station the train only goes one way (it's the last station in the line), so watch for the signs for which train is departing next. From the blue line you can connect to any of the elevated or L train lines. 

From Midway Airport

The Orange line will take you into the city and can connect you to any of the L trains. 

The Chicago transpiration system is one of the easiest I have come across. The system is designed like spokes on a wheel. So if you are downtown you can get just about anywhere in the city on the L. 

Where To Go - There is so much to see and do in Chicago, so here a couple of places that I have enjoyed when visiting the Second City.

John Hancock Observatory (now 360 Chicago). Open every day from 9am to 11pm you get an unbelievable view of the city. Adult admission for the ride up and the view is $19.

Or you can visit the Willis Tower and walk out on the ledge of Chicago's tallest building. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck. Day of tickets will set you back $30, order online and get a discounted rate of $19.50 for adults.

Free architecture walking tours are a great way to get some general knowledge of the city and appreciate the beautiful and not so beautiful buildings in the city. Free Tours By Foot has many types of tours to choose from such as food, ghost and the Lincoln Park Zoo. Be sure to book ahead of time and tip your guide!!

Wrigley Field

Book a tour of Wrigley field for only $25 per person. Stroll through the home of the Chicago Cubs and get the chance to see what happens behind the scenes of the Friendly Confines. This 70-90 minute tour will take you behind the scenes and see the visitors clubhouse, Cubs clubhouse, Cubs dugout and the historical Wrigley Field. Catch a game if you can!

NPR's Wait Wait Don't Tell Me taping

See the live taping of the radio program taped in the Chase Bank auditorium. $30 will get you a ticket to two of the funniest hours on your trip. Click the link for more information and tickets. 

Chapel in the Sky

Visit the Methodist church at the Chicago Temple Monday through Saturday a free tour is offered at 2pm.  At the corner of Washington St and Clark St on the 23rd floor is the tallest church building in the world. The views aren't spectacular, but it's an interesting and historical chapel.  

Second City Theater Troupe

Have a laugh with the best known, first ever, on-going improvisational theater troupe in the United States. Get tickets in advance Check groupon.com and goldstar.com for discount tickets. 

Where To Stay

Chicago Hostel International - located at 24 E Congress Pkwy. A 3-minute walk from Harrison subway station, this trendy hostel in The Loop is a 9-minute stroll from Grant Park, and a 15-minute walk from the observation deck of Willis Tower. Free breakfast buffet, WiFi and two cafe's on site. This hostel also offers private rooms.


Parthenon Hostel - located at 312 S Halsted St, it's just outside of the city center Chicago. A 15-minute walk from the Willis Tower, this modern Greektown hostel is 0.2 miles from an El train stop with 3-minute service to the Chicago Loop. Complimentary breakfast and all day coffee and tea with a restaurant and bar on site. Free WiFi of course.
Aloft - located 515 N Clark St, just north of the river. This contemporary, glass-sided hotel in the trendy River North area is a 6-minute walk from Michigan Avenue's high-end shopping and 1 mile from 360 CHICAGO's observatory. 

Where To Eat

Get your deep dish Chicago style pizza fix at Uno's Pizzeria. It's the best deep dish I've ever had! A small pan will serve two to three people. Or try Deu one block away, the 2nd Chicago style pizza joint. 

Enjoy a night on the town at RPM Italian. Serving traditional and modern Italian food in a sleek urban environment, it doesn't disappoint. Devour a big bowl of Mama DiPandis spaghetti and defiantly have the hazelnut tartufo for dessert. Don't skip on the dessert!!

Celebrate the end of prohibition at Berghoff. Enjoy a beer at the first establishment to get their liquor license after the end of prohibition. 17 West Adams street.  

Have a drink at The Trump Tower. Enjoy a cocktail while overlooking the Chicago river in the heart of downtown. 

View from The Trump Tower

I hope you enjoy The Windy City as much as I do. There is so much to do and see in this town, you wont be bored!