The Perfect 3 to 4 Days in Chicago Itinerary

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by Olivia Ellis

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Chicago, standing as the third-largest city in the United States and the unofficial capital of the Midwest, is a blend of refinement, American industriousness, diversity, and a sincere, laid-back Midwest vibe. Whether you’re planning a 3 or 4 days in Chicago itinerary, this guide will offer you everything that creates the Windy City’s unique identity, from its classic foods, to the historic architecture lining the city.

How Many Days in Chicago?

Chicago is a vast city and spending at least 3 days in the city is best to fully appreciate its diverse neighborhoods, iconic landmarks, and cultural institutions such as the Magnificent Mile, Millennium Park, and Lou Malnati’s Pizzeria.

Beyond this, 4 days or more in Chicago provide opportunities to dive deeper into Chicago’s neighborhoods such as Lincoln Park and Wrigleyville, or to explore at a more leisurely pace. Despite its size, Chicago is best enjoyed slowly, allowing you to get to know the city on a more intimate level.

Another component to factor in when deciding how long to spend in Chicago is the time of year. While winter in Chicago is famous for its blustery, snowy, and cold weather, the spring and summer open the city to an exciting atmosphere, with riverside events, beer gardens, and an abundance of outdoor activities such as city kayaking, or even swimming in Lake Michigan.

Because of this, I’d recommend spending more time in Chicago in the warmer weather vs a shorter trip in the winter unless you don’t mind spending time at your accommodation or your budget allows for time spent in a larger number of restaurants, or indoor sites/attractions.

Chicago Skyline from Lincoln Park
Chicago Skyline from Lincoln Park

Getting To & Around Chicago

Chicago serves as a major transportation hub in the United States, offering convenient access for both domestic and international travel. Chicago O’Hare, as the primary airport for the city and the state of Illinois, is often the most common arrival airport.

Alternatively, if you’re visiting from destinations within the Americas (from East Coast cities like Boston or Philadelphia or western cities like Los Angeles or Phoenix) or are flying with specific international carriers, you may also land at Chicago’s Midway Airport.

Both airports provide CTA Train services into downtown Chicago, making your journey into the city speedy and affordable compared to pricey taxi or ride-sharing services. From O’Hare, the journey takes approximately 45 minutes depending on your final destination.

If you need to reach downtown from Midway Airport, expect a shorter 25-minute train ride.

In addition to its airport accessibility, Chicago also boasts convenient train connections, particularly for travellers exploring the Midwest.

For those seeking to economize or are interested in exploring other Midwest cities like Indianapolis, Detroit, Cincinnati, or Milwaukee, Amtrak offers a comfortable Midwest route connecting these cities at a lower cost than air travel.

On a grid system layout, Chicago is renowned for its efficient public transportation and easy navigability, offering convenience and accessibility. Many central sites and downtown areas are conveniently within walking distance, making exploration of the city simple and convenient.

During the chilly winter weather, or if you just prefer to use public transportation, Chicago’s public transportation is excellent, providing a convenient means of moving around the city.

The Chicago Transit Authority (CTA) offers an extensive network of buses and trains, and even water taxis in the warmer months, allowing convenient access to Chicago’s diverse neighborhoods and sites.

Chicago CTA Train
Chicago CTA Train

3 to 4-Day Chicago Itinerary

Whether you’re keen to eat your way through Chicago, explore the city’s rich sports culture, admire its unique blend of architecture, or spend time wandering through its many cultural icons, there is a lot to do on a trip to Chicago.

Day 1 – Magnificent Mile, Willis Tower & More!

Magnificent Mile

Day 1 begins in the center of the city in the Magnificent Mile neighborhood of Chicago.

The Magnificent Mile is a prestigious and bustling neighborhood located along Michigan Avenue in central downtown Chicago. Stretching approximately 13 blocks from the Chicago River to Oak Street, the neighborhood is renowned for its upscale shopping, landmarks, and atmosphere. If you want to explore this area with a guide, you can book a walking tour.

I find this area to be a wonderful spot to explore in Chicago first, as it defines the energy of the city while also offering great breakfast spots and well-known Chicago spots such as Willis Tower.

The Magnificent Mile
The Magnificent Mile

Skydeck at Willis Tower

One of the iconic buildings worth visiting while in the Magnificent Mile is the Willis Tower. Built in 1970 and originally known (and still referred to by locals) as the Sears Tower, the Skydeck at Willis Tower offers possibly the best views of the entire city.

The most renowned feature of the Skydeck is the Ledge, located on the 103rd floor, allowing you to experience the sensation of being suspended over Chicago’s landscape while enjoying incredible views of the Midwest capital city.

On the ground floor, you can enjoy an interactive experience that educates you in Chicago’s culture and history, all while in a fun environment.

Tickets and time slots for the Skydeck must be booked in advance, and adult admission starts at $32.

If you’re interested in visiting multiple attractions/experiences in Chicago, the Chicago CityPass or the GoCity Pass is a great way to save money.

Looking down from the Skydeck
Looking down from the Skydeck

Starbucks Reserve Roastery

After experiencing Chicago at its highest point, head back to the city’s streets and make your way to the world’s largest Starbucks, here in Chicago.

Whether you’re a coffee drinker, prefer tea or you’re somewhere in the middle, the roastery is an attraction in itself, encompassing 5 floors of various interest, from coffee, bakeries and cocktail bars, to immersive roastery experiences and even a roof terrace.

Chicago Architecture River Cruise

The classic Chicago Architecture River Cruise is a quintessential experience for visitors to the city. Whether you’re an architecture enthusiast or simply enjoy learning about Chicago’s history while taking in its incredible scenery, this cruise offers the ideal opportunity.

As you wind along the Chicago River, you’ll have the chance to learn more about the city’s architectural landmarks while enjoying one of America’s most famous cityscapes.

Tours are available year-round, with multiple companies offering varying lengths of tours led by knowledgeable locals. These tours typically last between 60 and 90 minutes and provide amenities such as comfortable seating, bathrooms, and heating in the winter.

Some even offer a full-service bar onboard. Tickets can be purchased online and are typically priced around $40 for adults, though prices may vary depending on the provider and time of year or day.

Day 2 – Millennium Park, Art Institute & Deep Dish Pizza

Millennium Park & Cloud Gate

Start your second day in Chicago by visiting one of the city’s most iconic landmarks: Millennium Park and its famous attraction, Cloud Gate, unofficially known as “the bean.”

Situated in the heart of the city within Grant Park’s northwestern section, Millennium Park spans 25 acres and was established in 2004 to commemorate the third millennium.

Today, it stands as a symbol of Chicago, boasting an impressive collection of public art, panoramic views of Lake Michigan’s shoreline, and the Cloud Gate sculpture by Anish Kapoor.

Spend time wandering around one of Chicago’s most beloved green areas, taking in the park’s fountains, art, structures, the Chicago Cultural Center and even possibly enjoying a skating session in the wintertime.

Nearby, you could also pop by to see the iconic Chicago theatre to glimpse another of the city’s most famous landmarks.

The Cloud Gate in Millennium Park
The Cloud Gate in Millennium Park

Art Institute

By this point on your trip, you’ve likely noticed that Chicago is a city synonymous with art. One of the best ways to delve deeper into this aspect of the city’s culture is by visiting The Art Institute of Chicago.

As one of the oldest and largest art museums in the United States, the Art Institute houses nearly 300,000 pieces of art, including works by Pablo Picasso, Edward Hopper, Claude Monet, and a diverse array of sculptures, prints, and drawings from around the world.

During your visit, you can learn more about the museum and its installations through free guided tours offered daily at 1:00 PM and 3:00 PM.

The admission cost for adults is $32, with discounted tickets available for children and seniors. They can be purchased online or you can also organise a guided tour.

Additionally, admission to The Art Institute is included in the CityPass for those participating in the program.

Lion Statue in front of the Art Institute
Lion Statue in front of the Art Institute

Chicago Pizza at Lou Malnati’s

The first food that probably comes to mind when thinking about Chicago is Chicago deep dish pizza, and there’s no better place to eat it than at Lou Malnati’s Pizzeria, a Chicago institution founded by the oldest family name in Chicago Pizza.

Taking pride in the pizzeria’s use of fresh ingredients and vine-ripened tomatoes, anything on the menu will likely be delicious, but I suggest ordering the “Malnati Chicago Classic” with sausage, cheese, and tomato sauce or the “Lou”, a vegetarian option with spinach, mushrooms, tomato, and a tasty cheese blend.

With over 50 locations in the Chicago metropolitan area, you’ll be hard-pressed to not find a location nearby. Regardless of where you go, there’s no doubt that digging into a gooey, cheesy deep dish pizza is one of the best things to do in Chicago and if you’re really a pizza lover then you can also join a pizza tour!

Day 3 – Riverwalk, Museums & London House Rooftop

Chicago Riverwalk

On your third day in Chicago, explore the city riverside by strolling along the Chicago Riverwalk, a scenic pedestrian path that stretches for 1.25 miles along the Chicago River.

The Riverwalk comprises four distinct districts: The Confluence, The Arcade, The Civic, and The Esplanade.

Along this picturesque route, you’ll discover lush greenery, restaurants, cafés, art installations, and seasonal performances.

The Chicago Riverwalk provides an ideal setting to unwind, relax, and soak in the city’s ambiance, making it a favorite spot for both locals and visitors and a true example of how to take advantage of city space. You can also learn more about its darker past on this walking tour.

Chicago Riverwalk Sign
Chicago Riverwalk Sign

Navy Pier or Field Museum of Natural History

Chicago offers a diverse array of museums and attractions, ensuring there’s something for everyone in the City of Big Shoulders.

For those seeking an immersive experience, Navy Pier is a must-visit attraction. Originally built in 1916 as a dock for freight and passenger ships, Navy Pier has transformed into an exciting spot with restaurants, bars, shopping, and entertainment options for all ages. Admission is free, and the pier is open year-round.

Alternatively, for a more traditional museum experience, consider visiting the Field Museum of Natural History. As one of the world’s largest natural history museums, it houses a large collection of artifacts and exhibits exploring biodiversity and human cultures.

From dinosaur skeletons to ancient artifacts, the Field Museum offers an interesting journey through natural history and anthropology. Tickets can be purchased online.

View from Navy Pier
View from Navy Pier

Drinks at London House Rooftop

Conclude your third day in Chicago at the renowned London House Rooftop bar. Perched atop the historic London House Hotel, this rooftop venue offers unparalleled nighttime views of the city’s iconic skyline.

Enjoy an elegant atmosphere and house cocktails as you take in the breathtaking vistas of the Chicago skyline. During the winter, cozy igloo capsules line the terrace, creating a festive atmosphere (reservations necessary).

Reservations are recommended in advance for popular times, and a smart casual dress code is in place.

Day 4 – Lincoln Park or Wrigleyville

Lincoln Park

If you’re spending 4 days in Chicago, consider exploring a neighborhood outside the downtown area.

Lincoln Park, located on the north side of the city, offers a leafy escape from the hustle and bustle of Downtown Chicago. Explore its residential streets lined with boutique shops and abundant food options.

Visit the neighborhood’s namesake, Lincoln Park, and learn more about various plant and flower species at the Lincoln Park Conservatory. Don’t forget to enjoy a lovely coffee or lunch at Floriole Cafe & Bakery.

Walking through Lincoln Park
Walking through Lincoln Park


For sports fans, spending a day in Wrigleyville is an exciting option for your last day in Chicago. This former working-class neighborhood, home to the Chicago Cubs, buzzes with activity, especially during baseball season.

During baseball season, the area offers an exciting atmosphere, boasting a wide array of sports bars and pubs.

Year-round, Wrigleyville offers a laid-back and friendly atmosphere with fun restaurants, seasonal outdoor concerts, film screenings, and even a farmers market.

And if you’re visiting during baseball season, be sure to buy tickets to a game to truly feel the soul of Chicago.

Where to Stay in Chicago

Moxy Chicago Downtown – Located in downtown Chicago, this hip, pet-friendly hotel is an excellent place to rest your head. It boasts 2 restaurants, air-conditioned rooms and an on-site fitness center.

The Hoxton – This upscale, central hotel in the West Loop district is another great option in the windy city. There are on-site restaurants and beautiful rooms along with a great rooftop swimming pool – perfect for the warmer months!

Chicago Getaway Hostel – This cool hostel is a great budget option in the city. Offering lots of dorms and private rooms, there is a good social atmosphere. inviting common areas and a central location.

Not quite what you’re looking for? Click here to browse more Chicago hotels!

The Midwest is an entirely understated region of the United States, and a visit to its capital, Chicago, is the perfect way to find your way into the heart of its rich culture, warm hospitality, and urban landscape.

Are you planning to visit Chicago? Have any questions about this itinerary? Let us know in the comments!

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Olivia is a writer for The World Was Here First. Originally from Michigan, USA, she is currently living in Athens, Greece exploring Europe and filmmaking. When she’s not travelling or writing, Olivia can be found cooking delicious new recipes from around the world, reading, and spending time outdoors.

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