Fun in the Windy City: A City Break in Chicago - GeekyTravel.com

Fun in the Windy City: A City Break in Chicago

Chicago is a great city to visit and explore. They have so many unique sites to see, places to visit and things to do. Today we are going to look at a few of the must do things if visiting Chicago for the first time. But before we do that lets take a look at some of the basics.

Where to stay: Anywhere downtown near the Magnificent Mile. This area is conveniently located near many major sites and attractions. It will also make finding a cab or using public transportation very easy. For the purpose of this article we’ll assume you are staying somewhere near the Magnificent Mile.

Navy Pier

The Navy Pier is a great place for everyone and is located within walking distance from the Magnificent Mile. They have many children friendly activities perfect for those with families to entertain. You can take the kids on rides or to the children’s museum, which is also a great place to grab a boat ride out into the lake. Take the short ride, you won’t need to be out too long and boat is the best place to see the city. When you are done with your activities there are many great bars and restaurants to grab a bite to eat. One of the best of these is Harry Caray’s, named after the famous Chicago Cubs’ announcer. Although the location at Navy Pier is great, the original Harry Caray’s on McKinzie Street is worth a stop for a dinner — a true Chicago gem and reasonably priced too!

Architecture Tour

If architecture is your thing make sure to take the Chicago Architecture Boat Tour. These tours typically run for 60-90 minutes and take you up and down the Chicago River, explaining the history and architecture of many of the buildings as you cruise along. These cruises are easy to find from the Magnificent Mile as you can grab a boat right off the Magnificent Mile at Wacker Street. It is just a short walk from many of the hotels and if getting in the water is not your thing, there is an option to take the architecture tour by bus. Hop on an open air bus and see many of the great sites of Chicago. Tickets tend to run about $40-$50 per person and you can find these tours in the same area as the boat tours.

Wrigley Field

If you are a sports fan a visit to the Chicago Cubs stadium Wrigley Field is a must. One of the oldest stadiums in all of baseball, there is so much baseball history here. The Cubs have been bad for a long time and tickets are typically cheaper on the secondary market than through the box office. If you are spending a few days in town try to catch a couple of games, one from inside the stadium and another from a rooftop deck. Rooftop deck viewing is unique to Chicago because the stadium is in the middle of a neighborhood. Property owners have built seating and decks for people to look into the stadium and watch the game. These tickets are typically all inclusive, including food and alcohol, and cost around $100. If you check Groupon you can usually find even better deals for select dates. Getting to Wrigley Field is easy by train, just take the Red Line to Addison Station. From the Magnificent Mile you will want to catch the red line at Grand Stop along State Street, just off of Michigan Ave.

Eat Deep Dish Pizza

Chicago is famous for its deep dish pizza and this is a must have meal while in Chicago. Pizzeria Uno claims to be the original creator of the Chicago deep dish pizza and their pizza is definitely worth trying, but our personal favorite is Giordano’s. They are located one block off the Magnificent Mile on Rush Street. The pizza takes time to cook, so you will typically place your order when you arrive at the restaurant even if your table is not ready. This way when your table is ready you won’t have such a long wait for your pizza.

Check out the amazing views of the Chicago from up high

The John Hancock Building on Michigan Ave is a great place to get a view from high above Chicago. Observatory prices are $18 for adults and $12 for children. There is a restaurant on the 95th Floor called the Signature Room which is a great way to see Chicago without paying an admission price. However, you will need to eat or buy drinks up there. The best way to see the view is to head up there either mid-afternoon or late at night and just grab a drink. The drinks are a bit pricy, but cheaper than admission to the observatory. We wouldn’t eating a meal up there as the food is decent but overpriced, you pay for the view really.

Listen to some Blues

If listening to great music is your thing check out some blues music while in Chicago. Even if you are typically not a fan of blues/jazz you will probably really enjoy the show. The musicians are great and put on quite a good show. There are many places to hear great music and our personal favorite is Blue Chicago on Clark Street. It is a bit of a walk from the Magnificent Mile, but it is worth the walk. The place is rather small so try arriving early if you want don’t want to have to wait for a seat. The advantage of the place being small is that every seat in the house is a good seat and puts you up close to the music.

A few other places to check out

If you are looking for a great meal check out Gibson’s Steakhouse. It is one of the best steakhouses in Chicago, although it can be very tough to get a reservation there. It can be very tough to get a reservation there. Here is a tip that not many people know, if you can’t get into Gibson’s try eating next store at Hugo’s Frog Bar. The restaurants are located right next to each other on Rush Street and Hugo’s serves a nice selection of Gibson’s steaks and they also have many great seafood choices. Hugo’s is typically easier to get a reservation and you can have the exact same steak you would at Gibson’s while also giving your group more seafood selections.

If you have time head to the lower level of Michigan Ave (for those that don’t know Chicago is a layered city with some streets having two and three layers) and check out the original Billy Goat Tavern. There are several Billy Goat Tavern locations throughout the city, but nothing compares to the original.

The menu is very limited and there is a great story behind the bar that the bartenders are always happy to share with the customers. Once in a while if they are filming a movie there may even be a live goat to greet you. Grab a Schlitz on tap and enjoy hearing about the curse of the Billy Goat.

With so much to see and do Chicago surely has something that everyone will enjoy.

The John Hancock Building on Michigan Ave is a great place to get a view from high above Chicago. Observatory prices are $18 for adults and $12 for children. There is a restaurant on the 95th Floor called the Signature Room which is a great way to see Chicago without paying an admission price. However, you will need to eat or buy drinks up there. The best way to see the view is to head up there either mid-afternoon or late at night and just grab a drink. The drinks are a bit pricy, but cheaper than admission to the observatory. We wouldn’t eating a meal up there as the food is decent but overpriced, you pay for the view really.

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About the Author: Michael Flynn

My name is Michael Flynn and I am a lifelong world traveler. I have visited over 100 countries and have stepped foot on each continent. I love to visit new places, meet new people, and try cultural foods.