5 Day Chicago Itinerary (Planned By a Local With Map)

👉 Jump to: Day 1 | Day 2 | Day 3 | Day 4 | Day 5 | Where to Stay | Map | Getting Around | Tips | FAQ

Planning a comprehensive Chicago itinerary is crucial to getting the most out of your trip to the Windy City.

With Chicago being the third-largest city in the U.S., there’s a lot of ground to cover. From world-class museums to famous attractions, shopping, dining, and exceptional entertainment, there is no shortage of stuff to do in Chicago during your 5 days in the city.

I’m a Chicago local, and I love showing friends and family everything Chicago has to offer when they come to town. I have the inside scoop and, in this itinerary for Chicago, I’m going to detail exactly how you should spend your time on your trip.

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5 Day Chicago Itinerary

Day 1 – Get to Know Chicago

Morning

For your first morning in Chicago, head over to the John Hancock building (also known as the John Hancock Center) in Streeterville to experience the 360 Chicago Observation Deck. Ascend to the 94th floor where you’ll be greeted with panoramic views of the city—hence the name “360 Chicago.” This is also the best place for skyscraper views of Lake Michigan.

If you dare, take a ride on Tilt—Chicago’s highest thrill ride. This ride will tilt you 1000 feet over the Magnificent Mile on N Michigan Avenue so you can take in the city from a new (and slightly nerve-wracking) perspective. 

Then, wander down the Magnificent Mile to shop your heart out (don’t forget a reusable bag!). Hit up stores like The RealReal and Saks Fifth Avenue, as well as American Girl Place and the LEGO Store for kids. 

When you’re ready for a pick-me-up, stop by the Starbucks Reserve (this is the largest Starbucks in the world) for coffee and a light meal. If you go, be prepared to potentially wait in a long line.

👉 Pro Tip: Put on some comfy walking shoes for your Chicago trip, and check out our complete Chicago packing list for tips on what to bring.

Afternoon

When afternoon rolls around, board a Chicago architecture river cruise from the Shoreline Sightseeing docks at the end of N Michigan Avenue (Magnificent Mile). For over an hour, you’ll cruise along the Chicago River and pass more than 40 buildings including famous architectural sights.

After your river cruise, you’ll probably be hungry. From the docks, walk a few blocks to The Dearborn for a late lunch of fish and chips and parmesan truffle fries. Once you’re done with your meal, walk a couple blocks down W Randolph St to Millennium Park. 

It’s time to see Cloud Gate, aka the Bean! Snap some iconic photos and gaze into the mirror-like surface to see a reflection of downtown Chicago. Next, spend some time exploring other Millennium Park attractions like Crown Fountain and Lurie Garden. 

If you have time, walk across the street to see the world’s largest stained-glass Tiffany dome at the Chicago Cultural Center. The entrance is free and there’s a great gift shop to stop in before you head out.  

Evening

In the evening, take the train (the Pink Line) to the West Loop and have dinner at an iconic Chicago restaurant like Girl & The Goat or Smyth and The Loyalist. But be sure to make reservations first. If you’re feeding a crowd, head to Time Out Market to get a taste of the city’s best foodie offerings. 

👉 Pro Tip: To save some money, consider purchasing a Chicago CityPASS. For a fixed price of $114 for those 12+ and $93 for children ages 3-11, you’ll get access to seven attractions, including the 360 Observation Deck and other attractions included in this itinerary. 

Day 2 – Wander Museums or Head to Wrigley Field

Morning

For breakfast or brunch, make reservations at Beatrix in the West Loop. Here, you’ll enjoy a hearty and delicious meal, and fuel up for a day of more walking and wandering. 

Afternoon & Evening Option 1: Museums

If you’re a lover of arts & culture, then spend the majority of day 2 of your Chicago itinerary at either the Art Institute of Chicago or at Museum Campus.

For a world-class collection of art, head over to the Art Institute of Chicago (which is included in the CityPASS). Located in Grant Park just below Millennium Park, the Art Institute houses nearly 300,000 works of art from around the world and throughout history. 

If art isn’t your thing or you’re looking for something more interactive, opt for a fun-filled, educational afternoon at Museum Campus (this is also included in the CityPASS). For families with kids, an afternoon spent here is the way to go. 

Museum Campus is a 57-acre park that houses three of Chicago’s largest museums: Shedd Aquarium, Adler Planetarium, and the Field Museum of Natural History. It’d be hard to hit all three in one afternoon, so I’d recommend sticking to one or two.

After spending the afternoon at the museum/s of your choosing, head to Cindy’s Bar in the Loop for happy hour (but make reservations first). Cindy’s has one of the best rooftops in the city and will provide you with breathtaking views of the Chicago skyline, Millennium Park, and Lake Michigan.

If you’d rather skip happy hour and head straight to dinner, head to the Chicago River area and have dinner overlooking the water. Pizzeria Portofino and RPM Seafood are good options.

Afternoon & Evening Option 2: Wrigley Field

Sports lovers, spend the afternoon enjoying one of Chicago’s favorite teams—the Chicago Cubs at Wrigley Field. If you’re coming from the Loop, reach the stadium by taking the Brown Line to Belmont or the Red Line to Addison. 

Once you’re at the arena, snap a picture of the iconic marquee outside, and then enjoy a fun afternoon of cheering on the Cubs! If it’s baseball season and there’s a game going on while you’re in town, hitting up Wrigley Field is definitely one of the best tourist attractions and experiences in the Windy City.

After your game at Wrigley Field, head to nearby Murphy’s Bleachers for a drink and Chicago-style hot dogs. If you need a more family-friendly dinner option, D’Agostino’s Pizza and Pub is just a couple of blocks away from the stadium and serves up both thin-crust and deep-dish pizza. 

🏛️ Looking for more museums? Read all about the 20 best museums in Chicago.

Day 3 – Explore Lincoln Park and Old Town

Morning

After breakfast on Day 3, hit the Lakefront Trail at the edge of Oak Street Beach (for a longer walk, start at Navy Pier) and walk north up to North Avenue Beach. Here, you can walk out on the North Avenue Beach Pier and take beautiful photos of the downtown Chicago skyline behind Lake Michigan’s bright blue waters. 

Next, take one of the short tunnels underneath the road or cross the overhead bridge to reach Lincoln Park. Spend the rest of your morning enjoying all that Lincoln Park has to offer. Wander the park and nature boardwalk to begin. 

Then, head over to check out the animal exhibits at Lincoln Park Zoo (which is free). The Regenstein Center for African Apes as well as Small Mammal and Reptile House are some of the best exhibits. There are also interactive exhibits for kids to enjoy. 

If you’re looking for other activities to do in Lincoln Park, check out the Lincoln Park Conservatory and Alfred Caldwell Lily Pool (these are both free). The Chicago History Museum is also located in Lincoln Park and has ticketed entry.

Afternoon 

After filling your morning with some nature and wildlife, head into the Lincoln Park neighborhood for shopping and lunch. Lincoln Park has a bunch of great dining options such as Galit, Summer House Santa Monica, and Blue Door Farm Stand.

Once you’ve refueled with a tasty meal, head back out into the neighborhood to shop at local boutiques and wander by some beautiful homes.

Evening

Towards the end of the day, take the bus or walk (if you happen to be nearby) down to the neighborhood of Old Town. Here, you’ll top off the evening with a couple of hours of laughter at The Second City comedy club. There are shows happening every night of the week so if you book tickets ahead of time, there shouldn’t be any shortage of shows (or laughter, for that matter!) 

If you want to make dinner plans for before or after the show, the Italian restaurant, Topo Gigio, and the Mexican restaurant, Adobo Grill, are good options nearby. As with any Chicago restaurant, call ahead for reservations.

📚 Related Reading: 18 Best Chicago Neighborhoods

Day 4 – Take a Leisurely Walk and Then Catch a Show

Morning Option 1: Chicago Riverwalk

After breakfast on Day 4, take a leisurely stroll on the Chicago Riverwalk. The 1.25-mile walking trail on the Chicago River will make you feel like you’re in the midst of the action.

At the end of the Riverwalk, walk ten minutes south along N Wacker Drive to see Chicago’s tallest building—Willis Tower (formerly known as Sears Tower). Head up to the 103rd floor to reach Skydeck Chicago and the Willis Tower Ledge (you can use your CityPASS for this). You’ll witness incredible, sprawling views of the city.

Morning Option 2: The Lakefront Trail 

If you’re looking to spend some more time along Lake Michigan, start your morning off by walking the part of the Lakefront Trail that runs parallel to Grant Park and Millennium Park. Stick to the Lakefront or wander into the parks if you choose. Be sure to make a stop at Buckingham Fountain.

Afternoon 

Spend your afternoon enjoying the things to do at Navy Pier, one of Chicago’s top attractions. If you’re traveling with kids, stop into the Chicago Children’s Museum to let them play and learn through interactive exhibits. Then, take a ride on the Centennial Ferris wheel. 

Adults, be sure to check out the Navy Pier Beer Garden or relax at Polk Bros Park and take in the stunning Lake Michigan scenery. If you get hungry while you’re here, pick up some Chicago-style hot dogs at America’s Dog & Burger, or sit down for a Chicago deep-dish pizza at Giordano’s.  

If you visit between Memorial Day and Labor Day on a Wednesday or Saturday, stay into the evening to see Navy Pier put on their free fireworks show.

Evening

What better way to end the evening than by seeing a show? For music, Buddy Guy’s Legends is a no-brainer. This is one of the best opportunities to enjoy classic Chicago blues and an evening of great music overall. 

If you want something family-friendly, get tickets to a Broadway show in the Chicago Theatre District. Here, you can get swept off your feet with Broadway performances and other incredible plays. 

If shows aren’t your style, head to River North for bars and nightlife! 

📚 Related Reading: Interested in more Lake Michigan activities? Read about the 14 best Chicago beaches.

Day 5 – Spend the Day in Hyde Park

Morning

After a hearty breakfast or brunch, get ready for a mini day trip down to one of Chicago’s most historically and culturally rich neighborhoods—Hyde Park. 

If you rent a car or are thinking about it, it’ll definitely come in handy for this trip to the South Side. However, the Metra train (this is different from the CTA train) and CTA buses do have routes that reach this neighborhood. If you choose to take the bus, take Bus 6 from State & Jackson and ride 19 stops to the S Hyde Park & 56th St stop. 

Afternoon

Once you get off the bus, walk five minutes over to the Museum of Science and Industry (MSI)—the largest science museum in America. Here, you can enjoy a variety of interactive and educational exhibits within the realms of science, industry, and history. MSI is also home to the only remaining building from Chicago’s 1893 World’s Fair. 

After you’ve gotten your science fill, walk about 10 minutes west to the University of Chicago’s campus. Spend an hour or so walking around and admiring the Victorian Gothic style architecture. 

If you have the time (and energy), check off one last afternoon activity by touring the Robie House, designed by famous Chicago architect, Frank Lloyd Wright. Tours are available Thursdays through Mondays. 

Evening

After all this walking, you’re going to be hungry. Finish up the evening and your last dinner in Chicago by having a meal at Virtue Restaurant, a Michelin star establishment that serves up delicious Southern cuisine.  

👉 Pro Tip: If you’re looking for other mini day trips just outside the city, Garfield Park Conservatory and Oak Park are great options.

Where to Stay in Chicago

Best Hotels 

All of these hotels are centrally located in The Loop and River North (the boutique hotel is in West Loop), making them convenient for attractions and sightseeing. Read our guide on where to stay in Chicago for more information.

• 🛌 Budget – Ohio House Motel
• 🏨 Mid-Range – Hyatt Place Chicago/Downtown – The Loop
• ✨ Luxury – The Langham Chicago
• 🛎️ Boutique – The Publishing House Bed and Breakfast

Best Neighborhoods & Areas

Chicago’s different neighborhoods give the city a unique flair. Each of these neighborhoods offer a little something different from the main, touristy downtown scene. Read our guide on the best Chicago neighborhoods for more information.

• Neighborhood 1 (Lincoln Park) – An overall lovely neighborhood with tons of green space, attractions, and free things to do. Great options for dining and shopping, and good for families.
• Neighborhood 2 (River North) – Close to downtown and the Chicago River. Lots of galleries, restaurants, and options for nightlife.
• Neighborhood 3 (West Loop) – Foodie central with incredible dining options. The area is industrial turned upscale and popular for those in their 20s and 30s. 
• Neighborhood 4 (Wicker Park) – Artsy neighborhood with great Chicago coffee shops, local shopping and dining, music venues, and fun things to do.

Chicago Itinerary Map

Here is a Google Map with all the stop, attractions, and hotels mentioned in this post.

How to Get Around Chicago

Chicago has a comprehensive system for public transportation. This includes CTA trains (or the “L” as many people call it) and buses. A CTA Ventra card can be purchased at all train stops as well as many drugstores and convenience stores around the city.

I recommend purchasing a new Ventra card and loading your desired amount through the Ventra app. If you’re only staying for three instead of five days, you can purchase a 3-Day CTA Pass for $15. You can read my full Chicago transportation guide for more tips.

Depending on where you are, the city is quite walkable, too. Trails like the Lakefront Trail and Chicago Riverwalk are great for exploring popular areas. 

As far as cars go, Chicago is pretty driveable. For car rentals, I recommend Discover Cars. We also have a guide on driving in Chicago, which includes local rules and tips.

With traveling and getting around anywhere, there are some general safety rules and tips to follow. Read more about Chicago safety here. 

Chicago Itinerary Planning Tips

Tip #1 – Visit during the summer for more activities

Although the summers can be hot, this is a great season for taking advantage of some of the best the city has to offer. Summer events and activities include swimming in Lake Michigan, seeing Navy Pier fireworks, and enjoying live music and Chicago festivals in the parks.

Tip #2 – Always make reservations if possible

Chicago restaurants book up—it’s a foodie city after all! To be on the safe side, I recommend always calling ahead or making reservations online (especially if you have a group). To get a feel for how early to reserve a table, check out some restaurants a few weeks before your trip.

Tip #3 – Download the Ventra app

As mentioned, you’ll need to get a CTA transit pass or Ventra card for getting around. If you want to avoid any hassle or just save time, download the Ventra app ahead of time and purchase your pass once your trip begins.

Tip #4 – Download any museum apps 

If you want that extra bit of in-depth information and storytelling, download some museum apps before your visit. The Art Institute of Chicago has a great mobile app and audio tour. The Field Museum also has an app available for download.

👉 Read Next: How do Do Chicago on a Budget

FAQs about Chicago Itinerary

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That’s it for my 5 days in Chicago Itinerary! Whether you’re in Millennium Park, shopping down Michigan Avenue, or enjoying some famous Chicago hot dogs, you’re sure to have a blast. For more midwest fun, we’ve got you covered with the 17 best day trips from Chicago.

I hope I’ve helped you plan the perfect Chicago itinerary.