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Destinations

Chicago Itinerary: How to Spend 2, 3 or 5 Days in Chicago

Rebecca Holland

Rebecca Holland

November 29, 2023

7 min read

Table of Contents

As the third largest city in the country, Chicago has tons to do. From world-class restaurants, museums, theater, and comedy to thousands of acres of parks, biking trails, and beaches, there truly is something for everyone. 

Summer in the city is perfection, as three million residents collectively shed their heavy coats and embrace the sun with long walks along Lake Michigan and outdoor dining that seemingly pops up everywhere—seemingly overnight as soon as the weather warms up. But there’s plenty to do in winter too, from museums to ice skating to cozy restaurants and jazz clubs. 

It’s cliche, but also true that Chicago is a big city with a Midwestern vibe. Whether you’re visiting with family, on a romantic getaway, or with a group of friends, there really is an activity for every kind of trip. 

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2-day Chicago itinerary: How to spend 2 days in Chicago  

Day 1: The best of Chicago

chicago river cruise.

Start your day with coffee downtown. Cafecito serves excellent Cuban coffee and breakfast sandwiches, Revival Food Hall has several breakfast options like a juice shop or pastries, and the small The Goddess & Grocer chain is a safe bet for coffee and breakfast to go. 

Take a mid-morning Chicago Architecture Center River cruise, a picturesque way to see the city and get acquainted with its sights and history. The boat tour ends at Michigan Avenue, where you’re steps away from the Art Institute of Chicago and Millennium Park, a giant park in the center of the city with a theater and fountains, sometimes called the “front yard of Chicago.” Spend a few hours at the art museum, then grab a Chicago-style hot dog at Millennium Park and visit The Bean, an art sculpture that reflects the city and is popular for selfies. If you’re up for it, head across the street to the Chicago Cultural Center to see the stunning stained-glass Tiffany dome––the largest in the world. 

After all that sightseeing, stop for a drink at Cindy’s Rooftop, the rooftop bar in the Chicago Athletic Association Hotel with views across Lake Michigan. The lobby bar is also nice and cozy in the winter when you can settle in by a fireplace and warm up with a mulled wine or coffee. 

From here, you have plenty of options for dinner. Restaurants in the Loop or River North are an easy walk, or you could take an Uber or public transit to the many restaurants and bars in the West Loop. In River North, visit the city’s oldest steakhouse, Gene & Georgetti, for a traditional Chicago experience or Avli for modern Greek cuisine and people-watching. In West Loop, Top Chef winner Joe Flamm dishes up excellent Italian-Croatian cuisine at Rose Mary, or grab one of the country’s most famous burgers at Au Cheval. Post-dinner, see a Broadway show, listen to live music at one of the city’s many jazz clubs, like Andy’s Jazz Club, Untitled, or The Green Mill, or go dancing downtown or in the Northalsted neighborhood (also known as Boystown). 

Day 2: Gold Coast, Lincoln Park, and the Lake

chicago beach.

Today you’ll explore Chicago’s North Side, starting in the Gold Coast neighborhood, known for gorgeous historic mansions and high-end shopping. Make your way from the Loop to the Gold Coast via Michigan Ave., window shopping along the way. 

Grab coffee and pastry at the Restoration Hardware cafe (don’t miss the giant chandelier) and spend some time strolling the neighborhood. Dearborn and State are especially pretty streets. 

Rent a Divvy bike (or take public transit) and ride 2.5 miles along the Lakefront Trail north to Lincoln Park. If it’s hot, you might want to stop for a couple of hours at Oak Street Beach or North Avenue Beach. At Lincoln Park, you can visit the free Lincoln Park Zoo and Lincoln Park Conservatory

Grab lunch at one of the dozens of Lincoln Park restaurants, ranging from pizza to fine dining. Get deep-dish pizza at Pequod's, Middle Eastern food at Galit (which also has a fantastic wine list), or go all out with a tasting menu at Esmé or Alinea (often named one of the best restaurants in the world). From here, you have several options. Catch a Cubs game at Wrigley Field, a comedy show at Second City, or continue north to the Andersonville neighborhood, where you can support local shops and restaurants along Clark St. 

3-day Chicago itinerary: How to spend 3 days in Chicago 

Day 3: Museum Campus and Navy Pier

Chicago museum.

After a day exploring neighborhoods and the lakeshore, today is all about museums. Museum Campus is home to the Field Museum, one of the world’s largest natural history museums; Shedd Aquarium, a huge indoor aquarium and research center with daily shows; and the Adler Planetarium, which was the first planetarium in the U.S. and is now a museum to all things space––don’t miss the immersive movies in the Sky Theater. All are large and take at least two hours to walk through, so pick one or two and break in between at the museum cafes or food stands on the lawn outside. 

After, head over to Navy Pier, a large pier with games, rides, shopping, and dining––you can walk or bike along the lake, take a bus, or take a water taxi in the summer. Here, ride the Centennial Wheel and eat Chicago-style pizza. Navy Pier is great for kids as it has tons of games, rides, a children’s museum, and boat-watching opportunities. 

If Navy Pier isn’t your thing, head to Wicker Park instead. Here you can join Chicagoans on the always busy patio at Big Star, drink some of the world’s best cocktails at Violet Hour, shop local bookstores and boutiques, and take in the historic architecture. 

5-day Chicago itinerary: How to spend 5 days in Chicago  

Day 4: Living local

Chicago neighborhood.

Now that you’ve seen the highlights, it’s time to explore some Chicago neighborhoods. Start the day in Hyde Park with a self-guided Obama walking tour, where you can see sights like where the Obamas first kissed, Barack Obama’s first apartment, his favorite bookstore, the family’s current home, and more. You can also visit the Robie House, one of Frank Lloyd Wright’s most famous creations, spend a few hours at the Museum of Science and Industry, or walk the beautiful University of Chicago campus. There are lots of great restaurants in Hyde Park. Some favorites include Virtue, Medici on 57th, Nella Pizza e Pasta, and Plein Air Cafe

In the evening, head to Wicker Park, Logan Square, or Andersonville. Wicker Park is a hip neighborhood packed with boutiques, restaurants, and bars. Andersonville is quieter but also has nice boutiques and antique stores and great restaurants and bars such as Hopleaf for mussels and a huge beer selection, Taste of Lebanon for a quick shawarma or falafel, Spacca Napoli for pizza, or Big Jones for southern food. Then there’s Logan Square, which is arguably the best food neighborhood in the city. If you travel for the food (and drink,  head here for drinks at Billy Sunday, Scofflaw, and dozens of other great cocktail bars, happy hour at Webster’s Wine Bar, and dinner at Lula Cafe, Daisies, Andros Taverna, Mi Tocaya Antojería, the list goes on… Really, in Logan Square, you can’t go wrong with food or drink. 

Day 5: Day trip to Oak Park or Indiana Dunes National Park

Indiana Dunes national park.

With a fifth day, head out of the city. If you want to see a cute suburb of Chicago or are an architecture buff or Hemingway fan, hop on the train and head to Oak Park. If you’re craving nature, rent a car and visit the Indiana Dunes National Park.

Oak Park is just ten miles west of downtown Chicago but feels far away. The village is home to the Frank Lloyd Wright-Prairie School of Architecture District, a concentration of 27 Frank Lloyd Wright Homes, the largest in the country. Tour his home and studio, which was sort of an experiment for the architect and features hints at what would become his signature Prairie School Style. Oak Park was also home to Ernest Hemingway as a child. Visitors can tour the Ernest Hemingway Birthplace and Museum to learn about Hemingway’s time as a war reporter in Spain, see childhood photos, clips of his books that have been turned into movies, and more. In downtown Oak Park you can shop at local boutiques and bookstores and grab lunch or coffee at the numerous cafes and restaurants. Best of all, Oak Park is at the end of the CTA’s Green Line and easily accessible from downtown Chicago. 

The peaceful coastline of the Indiana Dunes is just 45 miles from Chicago and was designated a national park in 2019. The main attraction is the huge, shifting sand dunes created by Lake Michigan’s wind and waves, but there are also wooded paths, wetlands, and prairies in the 15,000-acre park. With more than 50 miles of trails, there’s a hike for everyone, from sandy strolls to walks through the woodlands. Visit during migration season to see hawks, piping plovers, sandhill cranes, and more. Each year on the third weekend in May, the park plays host to a birding festival. You can also rent kayaks, take a horseback tour through the park, or just relax on the sandy beaches. 

Key Chicago travel details

Where to stay in Chicago

The Loop is the heart of the city’s business and theater district and is conveniently located near most major attractions. River North is just over the Chicago River and has dozens of high-end restaurants, happy hour bars, and nightlife options. Both are easily accessible via the CTA and are well served by Uber, Lyft, and taxis. If this is your first time in the city, base yourself in one of these centrally-located neighborhoods. 

The Chicago Athletic Association Hotel has rooms from around $200 in the winter to $400 in the summer. Freehand Chicago starts at $29 for a shared dorm to $171 for a private King room. And Hyatt Centric The Loop has room from around $150.

How to get around Chicago 

Chicago has a comprehensive transit system known as the CTA. The L is the rail system, and it’s very accessible from downtown, Lincoln Park, Wicker Park, and Wrigleyville; less so from Hyde Park and Andersonville or other neighborhoods on the far west, south, and north of the city. 

For most tourists, the L or CTA buses can get you where you need to go. The L costs $2.50 per ride (Chicago uses per-ride fares rather than fares based on distance), while the bus costs $2.25. You can also purchase a one-day CTA pass for $5, a three-day pass for $15, or a five-day pass for $20. Tickets and passes can be purchased inside L stations. 

If you’re taking a day trip to Indiana, rent a car for the day. Most major car rental companies have locations in the Loop. 

When to go to Chicago

Chicago shines in the summer and early fall, when people spend as much time outside as possible, at the beaches, walking on the Lakefront Trail, or hanging out in the numerous parks. That said, summer is also the busiest time to visit, and if you can handle cold weather and prefer to spend time indoors at museums and restaurants, fares and hotel rooms are significantly cheaper. 

Chicago is a big city with lots going on year-round, from conventions to sporting events to big-name concerts, the James Beard Awards, car races, and more. In the summer, events seem to multiply. Lollapalooza is one of the biggest events each year, but there’s also Taste of Chicago, and every neighborhood hosts their own block party one weekend each summer. 

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Rebecca Holland

Rebecca Holland

Freelance Writer

Rebecca is a freelance travel and food writer who has lived around the Middle East for the past decade, in Jordan, Iraq, and now Dubai. She wants everyone to visit this part of the world for the history, hospitality, and especially the food! She writes for AFAR, Food & Wine, The Guardian, and more, and is the founder of Curiosity Magazine.

Published November 29, 2023

Last updated December 21, 2023

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