The Ultimate 4 Day Chicago Itinerary (2024)

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Chicago is one of America’s greatest cities. With world-class museums, incredible observation decks, stunning architecture and the glorious Lake Michigan, Chicago is an absolute must visit destination. In this guide, I’ve shared how to spend the perfect 4 days in Chicago.  

If you have four days to spend in Chicago, then you’re in for a treat. This is an ideal amount of time to really get a feel for this beautiful city. Four days gives you ample time to see the highlights while also exploring further afield. Whether you’re spending a long weekend in Chicago or heading there as part of a bigger trip, the itinerary below shares the best things to see and do in Chicago.

Also known as the Windy City, Chicago is the perfect blend of a modern bustling city with a laid-back vibe. If you find the likes of New York too chaotic, Chicago might be more suited for you.

Chicago itinerary
Chicago River

I’ve visited Chicago more times than I can count and have family who live there. It’s one of my absolute favourite destinations in the world and I’m excited to share this 4-day Chicago itinerary with you. This itinerary covers off all the main sights and explores some of Chicago’s vibrant neighbourhoods, making it the perfect itinerary for those visiting Chicago for the first time.  

Best time of year to visit Chicago

The best time of year to visit Chicago is in the spring or fall months. This is when the weather is the most enjoyable and the crowds are not quite at their peak.

Chicago is known for its long, cold winters, so unless you enjoy the cold, it’s best avoiding the winter months (November to March). Most of the attractions will still be open in the winter, but you may find activities such as kayaking and the sunset cruise won’t be operating.

4 day Chicago Itinerary

The summer on the other hand can be a glorious time to visit Chicago, especially if you want to make the most of the beaches. However, this is also the busiest time of year to visit. I visited Chicago in July and couldn’t cope with the heat. The attractions were also incredibly crowded.

The shoulder season months of April, May, September and October are by the best time to visit Chicago. The weather shouldn’t be too extreme, and the crowds are bearable.

Is Chicago safe to visit?

Chicago has a reputation for being one of the most dangerous cities in the USA. This means many potential visitors question if it’s safe to visit Chicago. However, if you look beyond the headlines, most of the crime is in specific areas of the city. These areas aren’t where tourists visit and can easily be avoided.

The areas of Chicago which are popular with visitors and mentioned in the below 4-day Chicago itinerary are generally very safe. The downtown area itself sees little serious crime, and is patrolled by police. I’ve visited Chicago several times now with no issues. In fact, I feel safer walking around Chicago than I do London.

Having said that, as a big city, there is always the potential for crime to occur. It’s a good idea to follow some simple guidelines, especially if you’re travelling alone. This includes not walking around alone in the dark and making sure your belongings are in a safe place.

Chicago itinerary

How to get around Chicago

The Windy City has an extensive public transportation network (CTA) making it easy to get around. Here are some of the best ways to get around Chicago.

By foot: you can easily walk between most of the Chicago attractions mentioned in the below itinerary. Walking is a great way to experience a city and find hidden gems.

The “L”: Chicago’s Metro system is also known as the ‘L’ train. There is an extensive network connecting the downtown area with the neighbourhoods and suburbs. It’s very straightforward to use.

Divvy: Chicago is home to Divvy, a bike hiring service. It allows residents and visitors to easily hire bikes on an as needed basis. There are numerous bike stations around Chicago and it’s one of the largest networks in North America. You can hire by the hour or by the day. I’d suggest visiting the Divvy website to download the app and get setup before you visit. You’ll need to be confident to cycle through the city itself, but cycling along the Lakefront Trail is one of the best things to do in Chicago.

By taxi or Uber: If all else fails, you have the option of using Uber or hailing a taxi in Chicago. This can be very expensive, however, so it’s worth looking at the other options mentioned above.

Day One in Chicago

Chicago Architecture River Cruise

Begin your 4-day Chicago itinerary by embarking on the famous Chicago Architecture Cruise along Chicago’s river. Seeing Chicago from the river is one of the best ways to experience the city’s marvellous architecture and learn more about Chicago’s past, including the Great Chicago Fire. If you only do one paid activity in Chicago, make it the Architecture River Cruise.

The Chicago River Cruise is a great thing to do in Chicago
Chicago River Cruise

The cruise sails along the Chicago River past many of the city’s landmarks, such as the Old Post Office Building, The Tribune Tower and the Willis Tower. At the end, head out into the marina to get a view of the Chicago Skyline from Lake Michigan.

If visiting Chicago in the shoulder seasons or winter, wear plenty of layers on the boat as it can get very cold.

The Willis Tower (Sears Tower)

Next up is a trip to one of Chicago’s most iconic buildings – the Willis Tower (formerly known as the Sears Tower). The Willis Tower was the world’s tallest building until 1996. For a while it remained the tallest building in North America and the Western Hemisphere, but it’s now been surpassed by One World Trade.

Willis Tower Observation Deck is great for a Chicago itinerary
Willis Tower Observation Deck

Despite losing its title, heading up to the observation deck at the Willis Tower is an absolute must-do on any trip to Chicago. It’s one of the best ways to see the true scale of the city and its incredible skyline.

The observation deck is known as Skydeck Chicago and takes visitors up to the 103rd floor for unbelievable views of the city. One of the unique features of this observation deck are the glass floor booths. Visitors can stand on a clear floor with the city right below. It’s certainly not for the faint of heart but it’s one of the best things to do in Chicago.

If you’re travelling during busy periods, I’d recommend booking Skydeck Chicago in advance.

The Chicago Riverwalk

The Chicago Riverwalk is a picturesque promenade alongside the river in downtown Chicago. Although you’ve already seen parts from your River Cruise, a walk along the Riverwalk is an absolute must while in Chicago.

The pedestrian-friendly pathway runs along the south side of the river. It’s a scenic way to explore the city with plenty of places to sit and take it all in. It’s a vibrant, urban space with public art installations.

Include the Chicago riverwalk on your Chicago itinerary
Views on the Riverwalk

Dedicate a good hour to exploring the area and finding its hidden gems. The Riverwalk is lined with cafes and bars.

If you’re coming from the Willis Tower, I’d recommend grabbing lunch and eating it at the Riverwalk. There is a great food hall called Urbanspace which could easily be visited between the Willis Tower and the Riverwalk.

The Chicago Theatre

After enjoying the Riverwalk, take a short walk around The Loop area to see the iconic Chicago Theatre. The theatre is an architectural landmark in Chicago and it’s a great photo opp.

Chicago itinerary
Chicago Theatre

Chicago Food tour

Finish your first day in Chicago by joining a food tour to learn more about the famous Chicago food. Chicago has won many awards for its food and is renowned for having some of the best food in the United States. Joining a food tour is the best way to experience this, especially when you only have four days in Chicago.

This is the food tour I did. There was so much food on offer. I can’t recommend it enough.

Day Two

Millennium Park and Cloud Gate

Start your day nice and early and head to Millennium Park to see the famous Cloud Gate, AKA, The Bean. This area can get very busy, so I’d recommend getting there as early as you can.

Cloud Gate, or The Bean, is a famous sculpture known for its reflecting exteriors. It was installed in 2004 and quickly became one of Chicago’s most recognisable landmarks. The surface reflects and distorts visitors and Chicago’s skyline. You can walk underneath and through The Bean making it a fun and interactive experience.

Spend some time exploring other attractions in Millennium Park, such as the Jay Pritzker Pavilion and the Crown Fountain.

Visit the Bean on your 4 day Chicago itinerary
The Bean in Chicago

Grant Park

Right next to Millennium Park is Grant Park, another green space in Chicago. Wander through the park past the famous Buckingham Fountain and towards the Museum Campus. It’s a nice short walk to your next destination.

Museum Campus

Continue your 4-day Chicago itinerary by heading to the famous Museum Campus in Chicago. This picturesque area of Grant Park is home to iconic cultural attractions such as the Adler Planetarium and Field Museum of Natural History.

Use the afternoon to visit one or two of the famous landmarks in Museum Campus. Even if you don’t want to visit any of these attractions, I’d still recommend a walk to the area. It’s a beautiful spot and there are some fantastic views of the Chicago skyline.

Here are some options for things to do at the Museum Campus.

Adler Planetarium
The Adler Planetarium is dedicated to the study of astronomy and astrophysics. Founded in 1930, it was the first planetarium in the United States. The Adler Planetarium has a range of exhibits, interactive shows and films for visitors of all ages to enjoy. I really enjoyed my visit to the planetarium in Chicago. We attended a fantastic virtual stargazing experience which I couldn’t recommend enough.

Field Museum of Natural History
The Field Museum in Chicago is one of the most prominent natural history museums in the entire world. I’m not the biggest fans of museums, but this one is an absolute must. One of the most famous exhibits at the Field Museum is “Sue,” the most complete Tyrannosaurus rex skeleton ever discovered.

Chicago Skyline from Museum Campus
Chicago Skyline from Museum Campus

Shedd Aquarium
Chicago’s aquarium is great for visitors travelling with children. The famous aquarium is home to an array of marine wildlife and has many interactive shows and features.

Soldier Field
While in the area, consider a quick visit to see the famous Soldier Field, a large stadium near the Museum Campus and home to the Chicago Bears. You can admire the stadium from the outside or join a tour to explore the stadium.

Downtown Chicago by night

Chicago is one of America’s most beautiful cities, but it somehow gets even prettier at night. Head to the DuSable Bridge in downtown Chicago for one of my favourite night-time views of the city. Consider a walk along the Riverwalk and see the city from a different perspective.

For a cool bar, consider Two Dots and a Dash – they serve up some epic cocktails.

Chicago itinerary
Chicago River at Night

Day Three

Cycle the Lakefront Trail

Day 3 of this 4-day Chicago itinerary starts off by hiring a bike and cycling along the famous Lakefront Trail. This scenic trail is perfect for cycling or walking. It’s one of the absolute best things to do in Chicago. The trail stretches for 18 miles (29km) along the shores of Lake Michigan and boasts some stunning views of the Chicago skyline, Navy Pier and the lake itself.

I’d suggest hiring your bike at Navy Pier and cycling north towards Lincoln Park and North Avenue Beach. Remember to look back for beautiful views of the city.

Tip: hiring a bike is easy in Chicago. Divvy have bike racks all over the city where you can use your phone to hire a bike by the minute or the day.

It only takes about 20 to 30 minutes to reach the next spot on this list, but you can continue cycling for as long as you want and turn around at any point. I’d suggest going to at least Belmont Harbour before turning back to the next spot.

Chicago 4 day itinerary
Lakefront Trail on a rainy day

Explore Lincoln Park

Once you’ve dropped off your bike in one of the many Divvy bike racks, spend some time exploring Lincoln Park. This is one of Chicago’s most iconic neighbourhoods and is home to a range of boutique cafes and shops.

I’d highly recommend visiting the Chicago Pizza and Oven Grinder Company for lunch. Here, you’ll find their famous pizza pot pie – basically a pizza cooked like a pie. It’s one of the best places to eat in Chicago to experience a twist on the famous deep-dish pizza.

Don’t leave Lincoln Park without walking around the park itself. There is a boardwalk around the park through some ponds and marshes. It’s a lovely short walk. You’ll also find Lincoln Park Zoo here. It’s one of the oldest zoos in the country and has free admission. (Note: I don’t like this attraction, the animals are in very small enclosures and often look listless. If you’re an animal lover, I’d personally avoid the Lincoln Park Zoo).

The Chicago skyline from Lincoln Park
The Chicago skyline from Lincoln Park

North Avenue Beach

This is one of Chicago’s best beaches and it’s right next to Lincoln Park. If it’s a nice day, spend some time relaxing on the beach before walking or cycling back to downtown Chicago. It’s a great place to slow down and relax a little away from the city chaos.

Navy Pier

After your morning exploring Lincoln Park, head to the iconic Navy Pier. The pier stretches 3,300 feet into the lake and has an array of attractions and activities on offer.

Walk down to the end of the pier for stunning views of Chicago and the lake, visit the Chicago’s Children Museum or ride on the famous Centennial Wheel, a Ferris wheel right in the heart of Chicago. There’s plenty of restaurants and cafes on offer here too.

Navy Pier is also famous for its fireworks show. This magnificent show takes places regularly throughout the summer, you can find the latest timetable on the Navy Pier website.

Visit Navy Pier on your 4 day itinerary to Chicago
Navy Pier

Sunset cruise

End your day with a sunset cruise on Lake Michigan. As the sun sets, watch the Chicago skyline light up the sky. I’d recommend a sunset tour on the famous Tall Ship Windy around Lake Michigan.

Day Four

Culture morning

On the fourth and final day of this 4-day Chicago itinerary, you have a few options to see your preferred attractions.

For culture and art lovers, I’d recommend a visit to the Chicago Cultural Center and the Art Institute of Chicago. They aren’t too far away from each other so it would be easy to see both.

The Chicago Cultural Centre is a famous building in Chicago. Inside, you’ll find incredible architecture and a range of exhibitions and displays about Chicago’s history. Many of these are free to enter.

Just down the road is the Art Institute of Chicago, one of the oldest art museums in the United States. The museum has artwork spanning 5,000 years of human history. It’s also home to pieces of art from iconic artists such as Vincent van Gogh.

The Art Institute of Chicago is a must don your Chicago Itinerary
The Art Institute of Chicago

For sport fans, head to the famous Wrigleyville and visit Wrigley Field. Wrigley Field is home to the Cubs baseball team. It’s an impressive stadium and the neighbourhood itself is a lively destination to explore.

The Magnificent Mile

Spend your afternoon strolling down the Magnificent Mile, Chicago’s number one shopping destination. Even if you don’t want to shop, exploring the Magnificent Mile is a must while in Chicago. Admire the incredible architecture or eat in one of the many restaurants.

Sunset at The John Hancock Centre

Finish your day at the famous John Hancock Centre and head up to the 360 Chicago Observation Deck. There’s no glass floor here, but this Chicago Observation Deck offers incredible panoramic views. You also have the choice to upgrade your ticket to include TILT, a thrilling experience where guests are tilted forward 1,030 feet above the ground.

The 360 Chicago Observation Deck is one of the best places to watch the sunset in Chicago. Grab a drink at the Cloud Bar and watch the sun go down. It’s one of my favourite memories from Chicago.

Sunset at John Hancock Centre
Sunset at Chicago 360

Find live Jazz music

End your 4-day Chicago itinerary with visiting a jazz bar and enjoying live music. Chicago is renowned for its live jazz music and there are several amazing spots to choose from. Check out the best jazz clubs in Chicago.  

Other Chicago itinerary ideas

If you have some extra time in Chicago or want to swap something in the above 4-day Chicago itinerary, consider one of the below activities.

Museum of Science and Industry

This interactive museum is a fantastic spot for those with a curious mind and for families. The Museum of Science and Industry boasts a range of interactive exhibits covering topics such as space exploration, biology, weather and physics. I wasn’t expecting to enjoy my time here as much as I did. It’s a little way from downtown Chicago, so plan for this to take up a full morning or afternoon.


Chicago’s Chinatown is the second largest in the USA. This vibrant area is in Chicago’s South Side and provides a different insight into the Windy City. Chinatown’s streets are lined with colourful storefronts and restaurants selling authentic cuisine. I had some of the best dim sum of my life in Chicago’s Chinatown.

Explore the Neighbourhoods

Most visitors know Chicago for its famous downtown area, but the city also has several distinct neighbourhoods, each with their own unique charm. The above 4-day Chicago itinerary covers famous neighbourhoods such as The Loop in downtown Chicago, Lincoln Park and Wrigleyville, but there are a couple of others well worth exploring.

The Windy Ship in Chicago
Chicago’s Windy Ship

One of the most vibrant and trendiest neighbourhoods is Wicker Park. Known for its independent boutiques, eccentric cafes and a lively culinary scene, a visit to Wicker Park is definitively worth your time. The nearby Logan Square is another trendy neighbourhood in Chicago.

Relax on the beach

Being on the shores of the giant Lake Michigan, Chicago is home to several fantastic beaches. If you are in Chicago during the summer months, make sure to build in some time to head to the beach. As the lake is so huge, it honestly feels like the ocean sometimes.

One of the best beaches in Chicago is North Avenue Beach, which is near Lincoln Park and covered in the above itinerary. Another famous beach close to the downtown area is Oak Street Beach. It’s quite small but has some great skyline views. The Montrose Beach is a great option if you have a bit more time in Chicago.

Chicago Botanic Garden

The Chicago Botanic Garden is in Glencoe, North Chicago. It boasts 385 acres of land with a range of different indoor and outdoor gardens. These range from the Japanese Garden through to a selection of greenhouses with a range of tropical plants and flowers. I’ve visited a few botanic gardens around the world and this one stands out as one of the best. There are some great Chicago skyline views from the gardens outside too.

Kayak in Chicago

The warmer months bring the city of Chicago and its lake to life with a selection of water-based sports and activities available. One of the popular summer activities in Chicago is kayaking on Lake Michigan or the Chicago River. I’d recommend Kayak Chicago who offer both rentals and guided tours.

Helicopter flight

For the ultimate bucketlist activity in Chicago, consider a helicopter ride over the famous skyline. Fly past the famous Willis Tower and John Hancock Tower and see the city of Chicago from an entirely different perspective.

Views from Chicago 360
Views from Chicago 360

Where to stay in Chicago

Chicago is a big city and deciding where to stay can be a little overwhelming. If this is your first time visiting Chicago, it’s a good idea to stay in the downtown area. This means you’ll be close to all the major attractions mentioned in this 4-day Chicago itinerary. It’s worth noting that this area of the city is one of the safest areas too.

The Loop & Magnificent Mile areas

The most popular area of Chicago for tourists to stay in is The Loop. Right in the heart of downtown Chicago, this area is close to all the major attractions, bars and theatres. It’s a great option.

For a bit of luxury, consider the Hotel Renaissance, one of Chicago’s most luxurious hotels. Many of the rooms boast views of the Chicago River and the stunning skyline. For something more affordable, consider the Arlo Chicago which is right by Millennium Park.

If you’re on a budget, The Loop is home to Chicago’s Hi Hostel. I stayed here for two nights on one of my visits to Chicago. It’s a great little hostel with everything you need.

The Magnificent Mile is another downtown area with a few choices of hotels. Consider the Ivy Boutique Hotel for a good value stay.

River North

River North is one of the best places to stay in Chicago. It’s still close to all the main attractions, but it’s a little more removed from the busiest areas.

The Hampton Inn Suites in River North are a little more on the pricier side but have modern rooms with plenty of space. Another popular option is the Godfrey Hotel, which is a little cheaper but still a great option.

Chicago by night
Chicago by night


If you’re keen to stay away from the downtown area, consider a neighbourhood such as Wicker Park or Lincoln Park. Both are well connected with Chicago’s key attractions and you can be in downtown Chicago within 20 minutes.

For the vibrant Wicker Park, consider the Wicker Park Inn or The Robey. A fantastic budget option in Lincoln Park is the Chicago Gateway Hostel.

Where to eat in Chicago

Chicago is renowned for its incredible food and culinary scene. It’s even won several prestigious awards for having some of the best food in North America.

Below, I’ve shared some of my favourite places to eat in Chicago. This is by no means an extensive list of the best places to eat, it’s simply a few of my favourite spots. All these food places fit in nicely with the above 4-day itinerary.

Breakfast and brunch

One of the best brunch spots in Chicago is Wildberry. I eat here every single time I visit Chicago. It’s one of my absolute favourite places in the city. The menu here offers traditional American style brunch items such as waffles and pancakes, but the food is honestly delicious. The portion sizes are enormous too. Wildberry is right next to Millennium Park, putting it in a very convenient location. There’s often quite a queue to get in.

Another popular brunch spot in Chicago is Yolk. As the name implies, all the food on the menu revolves around eggs. It’s a similar menu to Wildberry, and while it’s an absolute must try on your trip to Chicago, I think Wildberry takes the crown.

The city of Chicago
Chicago skyline

Deep-dish pizza

No trip to Chicago would be complete without trying its famous deep-dish pizza. There’s an ongoing debate about which is the best deep-dish pizza in Chicago, but here are some must try restaurants so you can decide for yourself. The three most popular deep-dish restaurants are Uno’s, Giordano’s and Lou Malnati’s. My personal preference is Giordano’s.

Other popular spots loved by the locals include Nancy’s and Milly’s Pizza in the Pan.

Chicago Pizza and Oven Grinder is another absolute must try pizza in Chicago. Honestly, this is the best pizza I’ve had in my life. It’s not the traditional deep dish as it’s a pot pie, but it well and truly deserves a place on this list. If you’re not a deep-dish fan, consider trying this pizza pie as an alternative.

Pizza Oven and Grinder Chicago
Pizza Pot Pie

Food Courts

There are several food courts in downtown Chicago which are perfect for grabbing a quick lunch during your 4-day Chicago itinerary. One of the best food courts in Chicago is the Urbanspace food hall, which is home to a range of vendors. Another one of my favourites is the Revival food court.


Chicago is home to thousands of restaurants worthy of being mentioned. Here are just a few of my favourites.

Up first is the True Food Kitchen which serves up delicious “healthier” food, including plenty of vegan options. If you’re after a lighter meal or some vegetables, this is a must. If you fancy some Greek or Mediterranean food, try Taza Café, which has some of the best falafels I’ve had in my life. The Purple Pig is also a great Mediterranean themed restaurant.

Some more of my favourite restaurants include the Billy Goat Tavern, Beatrix and The Gage. Logan Square and Wicker Park also have some epic restaurants to choose from.


I can’t share my favourite places to eat in Chicago and not mention Stan’s Donuts. As someone who doesn’t particularly like donuts, Stan’s is truly a marvel to mankind. The donuts in Stan’s are SO good. I lose count of how many I eat when visiting Chicago. Try the Biscoff pocket donut, it’s the best donut I’ve ever had in my life.

Stan's Donuts
Stan’s Donuts – Biscoff

Is the Chicago CityPASS worth it?

If you’ve visited any major US city, you’ve probably heard of CityPASS. Once you’ve purchased the pass, you’ll have access to a certain number of attractions and sometimes even discounts on other attractions.

The Chicago CityPASS includes access to the Shedd Aquarium and Skydeck Chicago (the Willis Tower). You can also choose three additional attractions from the below:

  • Field Museum of Natural History
  • Art Institute of Chicago
  • Museum of Science and Industry
  • 360 CHICAGO Observation Deck
  • Adler Planetarium
  • Shoreline Sightseeing Architecture River Tour

The pass costs $134 USD for adults and $104 USD for children (Jan 2024).

The Chicago CityPASS is well worth buying if you plan to visit the attractions on offer and follow the above 4-day Chicago itinerary. You’ll no doubt save a lot of money. If the Shedd Aquarium isn’t high on your list of things to do, it’s still possible to save money with the pass.

For example, entry to Skydeck Chicago, the Adler Planetarium, Chicago 360 and a River Cruise comes in at around $141 USD (depending on the chosen cruise and time of year). That’s without the Shedd Aquarium, so you basically get that for free.

If you’re only planning to do one or two of the attractions, then no, the CityPASS Chicago is not worth buying. The best way to work out if it will save you money is to add up the entry cost for all the attractions you want to visit. You can then compare this with the cost of CityPASS Chicago and make the right decision for you.

I hope you’ve found this article sharing a 4-day Chicago itinerary helpful. It’s one of my favourite places in the entire world and is an absolute must-visit destination.

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Chicago Itinerary
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