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Long Weekend In Chicago : A 4 Days Itinerary

Updated: Jun 14, 2022

The Windy City took our breath away when we returned to it after 22 years and realized how much it has changed since! From the architecture to the Bean to the Riverwalk, we fell in love with this city and it has become one of our top recommendations of cities to visit in the US.

Where To Stay

The most common areas to stay in downtown Chicago is the Loop and the Magnificent Mile. We decided to stay at a Hilton Garden Inn in the Magnificent Mile as it was the most central to all the attractions we wanted to check out. We did not have a car while in Chicago as it was more convenient to walk or Uber than to try to drive through Chicago traffic and find parking.

What To Do

Our first stop in Chicago was the Bahai Temple, 20 miles north of downtown Chicago. The stunning architecture of Chicago's Bahai temple takes your breath away every which way you look. It is the oldest Bahai temple in the world and took 40 years to build. The intricate details and carvings throughout the temple rival those of ancient India. A must see while visiting Chicago.

Chicago is famously known for the Sears Tower (now called the Willis Tower) but the views that this building boasts now has competition from the Hancock Building. While it is not as tall as the Sears Tower, it's 94th floor observation deck still offers beautiful views of the Chicago skyline. Located in the Magnificent Mile, it has become an incredibly popular spot to view the sunset and the city night lights. Tickets for the observation of the Sears Tower and Hancock Tower are comparable in price and they both offer similar views of Chicago from merely 2 miles apart. We chose to visit the Hancock Tower as we had seen the Sears Tower over 20 years ago and the Hancock Tower was closer to our hotel on the Magnificent Mile. Aside from the observation deck, Hancock tower also has a mini ride called TILT, which tilts passengers outside 30 degrees, and they have a full bar called BAR 94.

Sunset over the Windy City

As the lights turn on...

While the city has changed immensely since we last visited 22 years ago, we were the most impressed with the Chicago Riverwalk. There is a beautiful path that allows you to walk right along the banks of the river for a few miles. There are numerous cafes and restaurants along the side of the river, and there are guided boat tours available as well. The most popular boat tour for tourists and locals alike is the Chicago Architecture Boat Tour. There are many companies that offer this tour, and most have good reviews and travel the same route so choose whichever company offers you the best deal. Our tour was with the Chicago Lakefront Cruises company and it was a 1.5 hr guided tour on a two-level boat along the Chicago River. We were enthralled by our guides commentary and loved learning about the unique Chicago architecture. Definitely a must-do in Chicago.

Aside from the architecture boat tour, there are many free walking tours available in Chicago as well. We did the Chicago Gangsters & Crime Walking Tour as well as the Chicago Loop & Millennium Park Walking Tour. The gangster tour took us along the Magnificent Mile and explained the history of Chicago's mafia gangs and how they influenced the growth of the city. The Loop tour explained all the significant buildings and landmarks in the downtown loop area and ended at the Bean. We liked the loop tour more as it was more engaging and provided a history that interested us more.

Yet another premier Chicago tourist attraction is Navy Pier, located along the shoreline of Lake Michigan. It is a popular shopping and eating destination, with an iconic ferris wheel that comes alive at night. The view of the Chicago skyline from the wheel is beyond spectacular. Besides the ferris wheel there are other carnival rides and games that are geared towards families with young children. We were thankful for the indoor aspect of the shopping and eating, as the pier can get especially windy, due to its location on the waters edge. During the summer, the pier hosts a fireworks show on Wednesdays and Saturdays at 9pm and 10pm, respectively.

View of Chicago skyline from the ferris wheel

Of course, no trip to Chicago is complete without visiting the Bean. Officially known as Cloud Gate, the Bean was created by Anish Kapoor and was completed in 2006. Its made of stainless steel plates welded together and polished to get rid of any seams. It beautifully reflects the Chicago skyline and is worth the visit. To avoid the massive crowds, try visiting early in the morning before 10am. If you visit, don't forget to walk underneath the bean for a cool view.

Most of Chicago's notable celebrities are all alumni of The Second City, a popular improv and sketch comedy venue. While the stars of the show are relatively unknown actors, we wouldnt be surprised to see them on Saturday Night Live or with their own standup special on Netflix in the coming years.

Where To Shop

The most popular place for shopping in Chicago is Magnificent Mile. Located along Michigan Ave, it ranges from various mid-range to high-end stores. It's a great place for window shopping or actual shopping depending on your budget ;). Along Magnificent Mile you can also find the Chicago Starbucks Reserve. There is usually a long line to get into this multi-level roastery, with different kinds of coffee-related food and drinks served on each floor.

A lesser-known but equally cool place to go shopping in Chicago is the Macy's located in the Marshal Field & Co Building on State Street. It takes up an entire city block and is the biggest Macy's in the world, with over 2 million sq ft of shopping space, and is known as the first department store ever created. The best part of this store is the Tiffany mosaic ceiling located in the center of the store. Covered in over 6,000 sq ft of TIffany glass, it is the largest glass mosaic of its kind.

What To Eat

Chicago is known for its infamous deep dish pizza and it did not disappoint. For a full rundown of our deep dish rankings read my other post about the 5 top pizzerias, but our top two must-eat picks were Giordano's and Pequod's.

Aside from deep dish, Chicago is also famous for Garrett's Popcorn. You can find a Garrett's Popcorn store on almost every street corner and it is renowned for its "Garrett Mix" a blend of cheddar cheese and caramel popcorn that is served fresh. We thought this popcorn was overrated and overpriced, as it did not stand out from the popcorn mixes we get at Costco at home.

"Garrett Mix" a blend of cheddar cheese and caramel popcorn

We also tried a few chain bakeries in Chicago, Goddess and the Baker and Stan's Donuts. Goddess and the Baker had two locations in Chicago, one of which was down the street from our hotel. They are known for their creative coffees and lattes, using glitter and fun flavors to make their lattes unique and colorful. The line was out the door when we arrived, and the coffees and pastries were well worth the wait.

Stan's Donuts is another popular chain with locations across the country. We went to the original Chicago Stan's Donuts and it did not disappoint. They had a variety of cake donuts and we loved the chocolate glazed one that was not overly sweet. They also had a few fun flavors of gelato, and we enjoyed the mango flavor.

While hotdogs are considered a classic American food, Chicagoans have managed to put their own twist on it. A Chicago-style hotdog consists of an all beef hotdog on a poppy seed bun, topped with chopped onions, dill pickle, tomato wedges, pickled sport peppers and a neon green pickle relish. Though it can be found all over the city, one of the most famous places to get a Chicago style hotdog is Portillo's, an Illinois chain that is famous for its Italian beef sandwiches, chocolate cake, and of course their popular hotdog. The meat eater of our family has always been a hotdog fan at heart and did not regret this impromptu stop.

Our final must-eat in Chicago is Eataly. A multi-level building full of Italian cafes, restaurants, and marketplaces, it has everything needed to satisfy your Italian cravings. We had breakfast and dinner there and bought fresh baked bread from their bakery. Some of the restaurants were casual counters where you could quickly pick up food on the go, while there were also some sit-down restaurants that tend to have longer waits around dinner time. We were satisfied with every meal we had there and loved the variety of selection, especially for vegetarians.

Hope these travel tips come in handy the next time you are in Chicago!


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