Looking to spend a long weekend or have a vacation to Chicago? Well the Windy City has a lot to offer whether you come for a few days or a week there are so many neighborhoods, attractions, amazing restaurants, and things to see and do there is a lot to keep you busy. My favorite Chicago Itinerary would probably take place in the summer or fall. The best time to go to Chicago in my opinion. 

On my recent trip to Chicago, I spent four full days sightseeing in Chicago and checking out some unique neighborhoods. If you are planning a trip to Chicago, love adventure, great local food, traveling solo, then this is the perfect Chicago itinerary. 

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4 Days In Chicago – Day 1 

The Morning 

360 Chicago  

Are you afraid of heights? Well this may be an interesting experience for you, butThere is actually so much you can do at 360 Chicago located at the John Hancock Center. If you are looking for wellness activities in Chicago, an adrenaline rush, and some of the best views of the city this is the place for you. Come to the 94th floor of the John Hancock Center aka 360 Chicago

The first morning I headed to 360 Chicago for sunrise Yoga. Having a space to meditate, look out over the city and Lake Michigan while doing something good for my body was the perfect way to start out my Chicago experience! 

Then came the scary part, continuing to conquer my fear of heights with the TILT. First, you stand in a section of glass that tilts over the city at 25 degrees, then 45 degrees as you tilt over the city looking 1000 feet over the streets below. 

The Afternoon Chicago Fireboat Tours Historical and Architectural Cruise  

There are many ways to see a city, but the best way to see Chicago is from the Chicago River. I tried three different types of tours on the river, but this one was the most unique. Take the Fred A Busse old red fire boat on Lake Michigan, through the canal lock, and wind through the Chicago River to learn about not only the history and architecture of Chicago, but also Chicago Fire history and the boat. 

This family veteran owned business is definitely one to support in the Windy City. Plus the guide was great, knowledgeable, and it gave you a well rounded history of the city as well as the architecture. 

 

Late Afternoon Finger Licking Foodie Tours  

I was on a mission to try my first Chicago deep dish pizza. So I decided to take a tour with Finger Licking Foodie Tours. I did a self guided version with an audio component to give me a little information of three of Chicago’s finest pizzerias. The tour brought me first to Gino’s East. This place is known amongst celebrities who even autograph the wall. Don’t worry, you don’t have to be famous to sign your name on the wall. This place love’s graffiti. I got a small deep dish cheese pizza here. It was so cheesy and the crust was magical. 

Next, I headed for a short 10 minute walk towards the first Pizzeria Uno that opened its doors in 1943. This time I got to try a special pizza with cheese and sausage. The manager told me they have been getting their sausage from the same local butcher since they opened. It tasted so good. I definitely knew I was going to save room for the third pizza. 

The third and last stop, thankfully for my waistline, was Lou Malnati’s. I loved Lou Malnati’s, but probably because I was able to sit and relax with my pizza for a bit longer than the other spots. Don’t worry, none of the pizza was wasted, I brought what I did not finish to my hotel and put it in the fridge. Don’t miss taking a Food tour during your time in Chicago.

Sunset and Chicago Architecture Foundation Center River Cruise Aboard Chicago’s First Lady 

The more traditional and famous scenic boat tour through the city for architecture lovers is the Chicago’s First Lady- Chicago Architecture Foundation Center river cruise and tour. This is definitely for architecture lovers, and goes more in depth than any other tour. Chicago Architecture Center partnered with the First Lady of Chicago to create one of the best architecture tours in the United States. Go at the end of the day to see the golden hour hit the buildings just right, and learn about the history surrounding the Chicago River. This is something you can only do seasonally! So I recommend the summer months. There are two floors, indoor and outdoor seating, as well as a snack bar with drinks. So you can escape the weather if it turns. 

Day 2 

Tour Starbucks Reserve Coffee Roastery 

Welcome to the World’s Largest Starbucks, not only that it is a Starbucks Reserve. This Starbucks Reserve is special because it is one of six Starbucks Roasteries. This 5 floor coffee lovers heaven, each floor has a unique menu of coffee and food you can only get here. Starbucks Reserve Roastery offers coffee tours, amazing views of the Magnificent mile, and even makes its’ own Nitro gelato. The bakery was by far my favorite part other than the coffee. Watching the bakers and cooks in action was definitely a unique experience. Here you can see the largest cask in the world where the beans are roasted and distributed to the different floors. The coffee roasted here is consumed here and is definitely a unique experience. 

Shop on Magnificent Mile 

Magnificent Mile offers over 400 retailers, tons of restaurants, and is a wonderful street to cycle down or walk to window show or blow the bank. Some of the most magnificent retailers line Michigan Avenue. This stretch is comparable to Beverly Hills Rodeo Drive. From high end shops, to Chicago Staple’s like Garrett Popcorn Shop and other Magnificent Mile restaurants there is definitely something for everyone’s taste here. 

Shedd Aquarium 

One thing I absolutely love about Chicago, is it is so easy to visit amazing museums as well as the Aquarium with CityPass. I was able to visit Shedd Aquarium, which has operated since 1930 and is a great attraction for all ages covered by the pass. The building and view is impressive. Included in the admission was a 4D experience movie, touching the sting rays or feeding them for $5 USD and a ton of amazing exhibits to learn more about marine and local wildlife. Plan to spend around 2- 3 hours here to get the entire experience

Field Museum 

Right next door to the Shedd Aquarium is the Field Museum, a perfect place to explore the natural sciences. The museum is best known for its dinosaur exhibits and being one of the best natural science museums in the world. My tip this place is huge, I mean half a million square feet huge, so plan what you want to see beforehand, and plan to spend 3 hours here if you want the full experience. The star exhibit is the Griffin Halls of Evolving Planet where you can see Sue, one of the most complete Tyrannosaurus Rex specimens in the world.  \

Head to the Winter’s Jazz Club For Live Jazz 

Winter’s Jazz Club just had reopened when I came into town and I am so glad i was able to catch a Paul Marinaro Quartet. The Winter’s Jazz Club actually hosts shows from various jazz musicians from across the USA and Chicago. They do charge around $20 USD for a show, plus have a $10 USD minimum drink purchase. I was glad to have the experience of watching jazz in a city with a rich musical history. 

Day 3 

Sarah Fay in front of Georgia Okeefe artwork in the art institute of Chicago.
Art Institute of Chicago

Art Institute of Chicago 

There are actually so many great museums in Chicago, so if you cannot make them all don’t be bummed. It is just another reason to come visit again. If you only have an hour or two the Art Institute of Chicago is in the center of Downtown and right in Millenium Park. Very convenient, the Art Institute of Chicago makes it easy for you to hit up pieces of art you cannot miss in under an hour. I personally loved the iconic American Gothic, A Sunday on La Grande Jatte by Seurat, and Nighthawks by Edward Hopper. 

Millenium Park and Cloud Gate 

After getting your fill of art, head to explore Millenium Park where you can see the iconic Cloud Gate aka The Bean. It is one of the largest public art installations in the world. Head to check out Crown Fountain and the public art there to cool off. A towering video LED art displays over a fountain and children playing in it. The artwork was designed by Catalan artist Jaume Plensa. 

After, check out the famous Cloud Gate aka The Bean, this archway is perfect for your selfie. While I was there we could not get close to it, but it was still a sight to see and perfect for photos. The park is huge and there are even parks in the park, like Maggie Daley Park. If you want to catch a concert, festivals and concerts can be found at Jay Pritzker Pavillion. 

Wrigleyville 

Whether you are in Chicago for a Cubs game, or not, it is nice to check out Wrigleyville, the famous baseball field. There are also a lot of restaurants, bars, and tours of the field you can visit. On game day if you don’t score tickets or bleacher seats, try getting on one of the Wrigley Rooftops where you can enjoy the game day atmosphere. Chicago’s Wrigley Field is one of the only parks completely surrounded by a residential neighborhood. It is definitely a site to see! 

Lincoln Park and Lincoln Park Zoo 

A short bike ride from Wrigleyville was the Lincoln Park neighborhood. I headed to Heritage Bicycle General Store for lunch and coffee. Here you can get your bike worked on, explore their shop, and get amazing food for brunch. The breakfast sandwiches were very good and they had interesting special concoctions of lattes as well. Lincoln Park is Chicago’s largest public park and there are a lot of places to explore. 

My favorite is the Lincoln Park Zoo. It is amazing because it is free and a great way to spend a beautiful summer or spring day. Lincoln Park is also close to North Avenue Beach, brave the waters of Lake Michigan and take a dip. 

Bike the LakeFront Trail 

One way to stay active on the road is biking to new destinations, if you have time take a bike and ride along the 18 mile paved Lakefront Trail. It goes from the northern suburb of Edgewater to Hyde Park. The trail also passes some great restaurants and waterfront hotspots like Shore Club, Lake Shore Cafe, and Castaways. 

Day 4 

Eat Your Way Around Chinatown 

The second oldest Chinese settlement in America is in Chicago. Also, it is one of the largest Chinatowns in the USA. I came for the food and headed to Minghin Chicago for one of the best Chinese restaurants. Then I got some baked goods at Qing Xiang Yuan Dumplings, and boba tea at Bingo Tea. One reason I came to Chinatown was for Ping Tom Memorial Park because it has a unique view of the Chicago skyline. This is definitely a part of any foodie’s Chicago Itinerary.

Explore Art Murals on 16th Street and Pilsen 

I heard Pilsen was a little bit eclectic with beautiful art murals, amazing Mexican food, and great thrift shops. If you love street art head to 16 th Street for one of the longest stretches of street art muralsAfter shopping at Pilsen Vintage, grabbing coffee at Cafe Jumping Bean, and visiting the home and public piece of art of artist Hector Duarte. 

Navy Pier 

While I heard most locals do not go near the Navy Pier, I absolutely loved the view of the city at night here. If you have children you can find the children’s art museum. Saturdays you can go to Navy Pier in the summer and light up under fireworks. Also, come to where the first ferris wheel ever debuted at the World Colombian Expo in 1893. Today, while you cannot ride the original you can ride a very tall ferris wheel. 

Urban Kayaks for the Adventurous Chicago Itinerary

Want to experience a little thrill while heading down the Chicago River? Add this to your Chicago Itinerary if you are an adventure seeker. A trip with Urban Kayaks through the Chicago River is an adventure and a great way to learn an entertaining history of the development of the River Walk, the history of the Chicago River, and learn about one of the most architecturally beautiful cities in the USA. It was fun trying to dodge the larger river cruises and getting to be very close to the Chicago River. Come during St. Patricks Day to see the river turn green!

One interesting fact about the river was how it was engineered to be reversed! It actually was reversed to flow against it’s original current towards St. Louis, Missouri. I was shocked to learn about this, but it is interesting to learn after my visit to St. Louis.

Watch Sunset At Skydeck and Get a Photo at the Ledge 

When I tell you the CityPass is the way to go when you are in Chicago, I am not lying. This is a great pass because not only does it get you into a ton of Chicago’s top attractions, it also lets you skip to the front of the line to things like the Skydeck. I saw this huge line and was in a rush. I thought I would be late for my next appointment, but I was able to get to the top of Skydeck for sunset and get some epic views of sunset on the Ledge. The Ledge hangs over a thousand feet in the air above Chicago. It was definitely a thrilling experience. Just make sure you have some ideas of how you want your photo to come out because you will have a limited amount of time on The Ledge. 

Where to Stay In Chicago 

Acme Hotel Company 

While there are a lot of great places to stay in Chicago, I wanted somewhere young, hip, and close to a lot of the attractions. I particularly fell in love with the ACME Hotel Company. I was right in the center of everything, the rock and roll decor, access to the city, a bakery/cafe on site, a popular restaurant/bar even with locals The Berkshire Room, and a great staff makes this the perfect place especially for a solo traveler looking to mingle. This was a perfect jumping off point for my Chicago Itinerary.  

The Room aka The King Suite 

My room was very spacious. I actually had a King Suite. The bedroom was separated from the living space where there was a couch, seat, microwave, mini fridge, and  another TV. I liked this because it was perfect for me to get some work done in the morning. 

The decor of the room was definitely fun, with pops of color, and unique design elements that added to the fun air of the ACME. I also loved the giant red lips on the bathroom mirror! 

Every morning, the staff of the hotel delivered branded canisters of coffee that you could take on the go with you as you explored the city. 

The Location

It was right near the amazing Pizzeria Uno, Eataly next door, and just a short walk from Millenium Park. I could not have asked for a better location. Also, it was close to Magnificent Mile where there are a ton of shops, restaurants,and a great place to take a walk. 

The Best Time of Year To Visit Chicago 

The best time of the year to visit Chicago in my opinion is the summer or fall. I loved my time visiting in May. The weather was already warm, sunny, and it was a great experience. I heard the fall colors in Chicago are also supposed to be lovely. However, if you go in the summer you can ride bikes, enjoy the parks, and even go swimming in Lake Michigan. Depending on the type of activities you want to accomplish, my favorite Chicago Itinerary would be in the summer months when the weather is sunny and warm!

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Getting Around Chicago 

Sarah Fay in front of the Chicago Theater
Chicago itinerary
Chicago Theater

L Train System 

The L Train system takes you everywhere you need to go. Even if you want to take the train from the Chicago O’Hare to Downtown Chicago you can grab the blue line to make the journey. 

Divvy Bikes

I took Divvy Bikes around the entire city, you could either get a day pass for $15 USD, or pay per ride $3.60. It was perfect to explore different neighborhoods, the parks, the lakefront trail, and enjoy the summer weather in Chicago. 

Chicago Greeters 


Chicago Greeters is a program that began with Choose Chicago and is perfect if you love to travel local. These are Chicago Locals who have donated their time to meet travelers visiting Chicago. They match you based on interests, availability, and neighborhoods you may want to explore. Be sure to put in a request 10 days in advance for an appointment with Chicago Greeters to make sure you get a tour. The tours are free and this is a great way to get around a neighborhood.

Whose planning their next Chicago Itinerary now?

Hopefully my Chicago Itinerary and travel guide will help you find some of the best things to do in Chicago. It also shows you how to see quite a lot of the city, with out breaking the bank. I particularly loved the CityPass and it helped me to narrow down my Chicago itinerary to make for an epic trip to Chicago. Also, if you are planning a trip be sure to save the Chicago itinerary on Pinterest below.

Plan your next Chicago Itinerary with this comprehensive travel guide to the Windy City from where to stay, what to do for food and culture!

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