Last summer my sister and I started planning our trip to this beautiful city. We booked an apartment on May through Airbnb, we booked the majority of our activities with time. We also had a private tour in Chicago (FREE) thanks to this website Chicago Greeter and let me tell you, it was an excellent experience, we did that on our first day.
The windy city has endless options for fine dining, cutting edge comedy, die-hard sports fans and let’s not forget about the largest contemporary art venue that is Museum of Contemporary Art.
I’m an architect student and going to Chicago was fulfilling. Chicago architecture has influenced the history of American architecture. The Great Chicago Fire destroyed many buildings in 1871. The city has managed to rise like a phoenix. Chicago’s skyline is one of the world’s tallest and ranks among its most magnificent. It boasts four of America’s eight tallest buildings.
Lake Michigan is the third largest of the Great Lakes. The lake touches Indiana, Illinois, Michigan and Wisconsin.
You can’t truly experience Chicago without a trip to Navy Pier. This 50-acre playground of entertainment, museums, activities, restaurants, and shops is the perfect place for some fun time.

Things you have to do and eat in Chicago:

1- Book a tour with Chicago Greeter 

It was an awesome tour, Daniel (our guide) planned out a great tour based on my love for architecture. He showed us a lot of great buildings and told us about Chicago History. It was so great to meet a local who is so passionate about his city.

2- Millennium Park

Millennium Park is a public park located in the Loop with 25 acres of awe-inspiring landscape, breathtaking architecture and iconic collection of public art, Millennium Park is Chicago’s premier green space. All year round, “The Bean” is an iconic draw for visitors and locals alike.

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3- Navy Pier

Navy Pier has so many things to offer from activities to food. The 150-foot Ferris Wheel, which offers great city and Lake Michigan views and it open year-round.

3- Garrett Popcorn
Handcrafted gourmet popcorn. They have different flavors, but the most popular one is the Garrett Mix (combines sweet Caramel Crisp with savory Cheese Corn).
4- Chicago-style hot dog
The hot dog is topped with yellow mustard, chopped onions, green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. We really like it.

5- Skydeck Chicago. Willis Tower

103rd floor of the former Sears Tower with clear observation boxes & views extending to four states. It was an amazing experience.

6- Chicago-style pizza. Giordano’s 

The famous STUFFED deep dish pizza. You certainly did not disappoint! We went for the Chicago classic deep dish consisting of pepperonis, mushrooms, onions, and green peppers. You can’t beat that classic combo! Takes about 45min to cook, so be sure put in your order right as your seated if you know what pizza you want then figure what you want for appetizers and drinks to reduce your wait time on the pizza coming out.


7- Oak Street Beach

This place which is a small piece of escape from the big cityscape that is the metropolis of the city of broad shoulders. A little stetch of beach that you may dream you’re someplace else and not in a really big city on a lake?  Still it’s a small strip of what makes this city nice even if there’s more beach on other parts of the city like North Ave but Oak street is special being so close to some of the nicest neighborhoods in town and being much smaller.

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8- Ride bikes
Renting bikes is super easy in Chicago ever since Divvy came along. For just $7 for the whole day, you can rent a bike. Divvy stations are located all along the lake front. However,  renters have to return their bike to a station every half hour or will be charged an additional dollar per half hour they don’t return it. If you don’t want to return bikes every half hour other companies like offer full day rentals.
9- Au Cheval
Excellent burgers, but the wait is LONG. We had to wait for 3 hours to get a table. Highly recommended you try this place. The burger was absolutely amazing, one of the best ones I had.
10- Chicago Architecture Foundation River Cruise
This is the best architecture-focused cruise in Chicago, no question. Worth every penny. It covers everything you need to know about the Architecture of Chicago and its Beauty. It was informative fun and a good way to get rest f you are a Tourist. It was my Highlight of the Trip. They have a full bar downstairs, You can purchase a bottle of champagne and enjoy it as you cruise around the city.
I went into it knowing a lot about Chicago history and architecture, but I still learned plenty. Our docent was knowledgeable and passionate about Chicago architecture, with some humor thrown in as well. All the CAF docents are volunteers and they know their stuff – these are not high school kids being paid minimum wage to read from a script. The tour departs from a dock at Michigan and Wacker, heads out toward the mouth of the river at Lake Michigan, north to Goose Island, south near Roosevelt Road and back to the dock. It was about 90 minutes long.
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I loved Chicago and I’m dying to go back!

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