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

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As a Chicago local, I love showing my friends and family everything the Windy City has to offer when they come to town.

With Chicago being the third-largest city in the country, there’s a lot of ground to cover! From world-class museums and famous attractions to plenty of shopping, dining, and exceptional entertainment, there is no shortage of things to do in Chicago.

This itinerary covers five days in the Windy City, taking you from all the bucket-list tourist attractions to local spots you might otherwise miss. If you’re crunched for time, I also wrote a 1 day Chicago itinerary. Let’s get into it!

Where to Stay for 5 Days in Chicago

For a 5 day visit to Chicago, these are my top picks for where to stay: 

• 🏆 My #1 Overall Pick – LondonHouse Chicago
• 🗺️ Best Location – L7 Chicago by LOTTE (full hotel review here)
• 🛏️ Best Budget – Freehand Chicago
• 🏨 Mid-Range – citizenM Chicago Downtown
• 💎 Best Luxury – ​​The Langham Chicago
• ❤️ For Couples – The Langham Chicago
• 🏠 Apartments – Find a Rental in Chicago

For more, check out my full guide to where to stay in Chicago.

🖨️ Get a printable version of this itinerary

Day 1 – Get to Know Chicago

Morning – See the Windy City From Above and Stroll the Magnificent Mile

For your first morning in Chicago, head over to the John Hancock building (officially known as “875 North Michigan Avenue” — but that’s a boring name imo) in Streeterville to experience the 360 CHICAGO. Ascend to the 94th floor to the observation deck where you’ll be greeted with sweeping views of the city and Lake Michigan. 

If you dare, take a ride on Tilt. This “ride” will tilt you 1,000 feet over the Magnificent Mile on N Michigan Avenue so you can take in the city from a new (and slightly nerve-wracking) perspective. 

Back on the ground, wander down the Magnificent Mile to shop your heart out. You’ll find everything from The RealReal and Saks Fifth Avenue to Zara, Uniqlo, and Nike. If you’ve got kids in tow, don’t miss American Girl Place and the LEGO Store (located inside Water Tower Place). 

When you’re ready for a pick-me-up, stop by the Starbucks Reserve (fun fact: this is the largest Starbucks in the world!) for coffee and a light meal. Just be prepared to potentially wait in a long line, as other folks have the same idea. If the line’s unreasonably long, head a couple blocks off the Mag Mile and pop into Eataly or Goddess and The Baker instead.

👉 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 – Architecture Cruise, Millennium Park (and The Bean), and the Chicago Cultural Center

When afternoon rolls around, board a Chicago architecture river cruise from the Shoreline Sightseeing docks at the end of the Magnificent Mile (N Michigan Ave). For over an hour, you’ll cruise along the Chicago River and pass more than 40 buildings including famous architectural sights. It might seem like a touristy thing, but it’s truly worthwhile even if you don’t consider yourself an architecture aficionado. 

After your Chicago river cruise, you’ll probably be hungry for a real meal. From the docks, walk a few blocks southwest 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 east 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. Then, stroll the park and explore other Millennium Park attractions like Crown Fountain, the Pritzker Pavilion, and Lurie Garden. If you have young kids, head to the playgrounds at Maggie Daley Park.

Walk across the street to see the world’s largest stained-glass Tiffany dome at the Chicago Cultural Center. The entrance is free (this is also a good place to use the bathroom if needed) and there’s a great gift shop to check out.  

Evening – Dinner in West Loop

When evening rolls around, take the train (the Pink Line) to the West Loop. This part of the city is widely regarded as Chicago’s foodie neighborhood. 

Have dinner at an iconic Chicago restaurant like Girl & The Goat or Monteverde. But be sure to make reservations first! If you can’t snag a table at one of these spots, see my Chicago restaurant guide for more ideas.

Day 2 – Wander Museums or Head to Wrigley Field

Morning – Fuel Up With a Hearty Breakfast

For breakfast or brunch, make reservations at 3 Arts Club Cafe in Gold Coast. This beautiful restaurant (though pricey) is located within Restoration Hardware and features a stunning atrium. The food is good, but it’s worth it just for the ambiance. 

If you can’t get into 3 Arts Club Cafe, try Luxbar. It’s also in Gold Coast and has an old school feel.

Afternoon & Evening Option 1: Chicago Museums

Are Chicago’s museums a priority for you? Then you’ll want to choose this option. 

If you’re a lover of arts & culture, make a beeline for 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. 

You’ll want at least a couple of hours perusing the many rooms. My favorite parts of the museum include the Impressionism wing, Art of the Americas, and Arts of Asia. But the hall of sculptures and the exhibit on Egyptian history are worth stopping by, too. 

On the other hand, families with kids might prefer the museums at Museum Campus over the Art Institute. Museum Campus includes the Shedd Aquarium, Field Museum of Natural History, and Adler Planetarium (also in the CityPASS). For families with kids, an afternoon spent here is the way to go. 

Full transparency, it’d be nearly impossible to hit all three in one afternoon, so I recommend sticking to one… maybe two. And if I had to choose just one, I’d pick the Shedd Aquarium.

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 gorgeous 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! 

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. 

Of course, it’s not always baseball season. So, depending on when you find yourself in Chicago, consider a Bears game at Soldier Field or a Bulls or Blackhawks game at the United Center. 

Day 3 – Explore Lincoln Park & Old Town

Morning – Lakefront Trail and the Lincoln Park Zoo

Wake up a little early and fuel up with a hearty breakfast. This day involves a lot of walking!

Hit the Lakefront Trail at the edge of Oak Street Beach and walk north up to North Avenue Beach, one of Chicago’s most popular beaches. 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 pedestrian 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 along the South Pond to begin. 

Then, check out the animal exhibits at Lincoln Park Zoo. Entry is free and you can just walk right in. 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’ve still got some pep in your step after all this walking, head over the Lincoln Park Conservatory. It’s free to enter, but online reservations are required. 

☔ Pro Tip: If it’s raining, head to the Chicago History Museum instead. 

Afternoon – Lunch, Shopping on Armitage Ave, and a Neighborhood Stroll

After a packed morning of nature and wildlife, head into the Lincoln Park neighborhood for lunch. Try Cafe Ba-Ba-Reeba or Summer House Santa Monica (snag reservations if possible). For something more casual, head to Small Cheval or Spoko. 

Once you’ve refueled with a tasty meal, do a little shopping in Lincoln Park. The intersection of Armitage Ave and Halsted St is a good place to start. 

Be sure to wander down some of the residential side streets while shopping and exploring Lincoln Park. The neighborhood is full of beautiful homes — old and new — with interesting architecture. 

Evening – Dinner and a Comedy Show

Towards the end of the day, make your way down to the neighborhood of Old Town, which is just south of Lincoln Park. 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.

📚 Related Reading: 18 Best Chicago Neighborhoods

Day 4 – A Scenic Walk, Navy Pier, and a Show

Morning Option 1: Chicago Riverwalk

Feel free to sleep in a little since Day 3 was a long one. After you get some breakfast, take a scenic, leisurely stroll on the Chicago Riverwalk. Admire the architecture and soak up the beautiful cityscape.

At the end of the Riverwalk, walk 10 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 & Grant Park

If you’re looking to spend some more time along Lake Michigan (I wouldn’t blame you, I love the lake), start your morning by walking the part of the Lakefront Trail that runs parallel to Grant Park. Stick to the Lakefront or wander into the park if you choose. And make a stop at Buckingham Fountain.

Afternoon – Navy Pier

Spend your afternoon enjoying Navy Pier. Yes, it’s touristy, but it’s worth a stop if it’s your first visit to Chicago. If you’re traveling with kids, pop 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 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 – Catch a Show

What better way to end the evening than by seeing a show? For music, Buddy Guy’s Legends is a no-brainer. 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 or West Loop for trendy bars and nightlife, or, Wicker Park and Logan Square for a more local going-out kinda feel.

Day 5 – Spend the Day in Hyde Park

Morning – Have Breakfast, Then Journey Down to Hyde Park

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. 

You can take public transit down to Hyde Park. But I’ll be honest, it’s a bit of a trek. If you don’t want the hassle, this is one part of the itinerary where I suggest taking an Uber, just for simplicity’s sake.

Afternoon – Explore the Museum of Science and Industry & Wander U Chicago’s Campus

Your first stop is the Museum of Science and Industry (MSI). It’s the largest science museum in America! Enjoy a vast array of interactive and educational exhibits within the realms of science, industry, and history. I’m talking about everything from medical exhibits to WWII history and even farming. Calling this place “massive” still feels like an understatement. 

By the way, the building that houses MSI is one of only two remaining buildings from Chicago’s 1893 World’s Fair! The other is the Art Institute. [Source]

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. 

While you’re at it, see if you can spot some famous movie scenes. For instance, the opening of When Harry Met Sally was at UChicago. And the Erudite Headquarters in Divergent was actually the university’s Mansueto Library.

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

Evening – Dinner at Virtue

After all this, 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 (just make reservations ahead of time!).

Map of Places Mentioned

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

How to Get Around

Chicago has a comprehensive system for public transportation. This includes CTA trains (also known as the “L”) and buses. A physical CTA Ventra card can be purchased at all train stops. You can also download the app and have it on your phone. 

I recommend purchasing a new Ventra card (real or virtual) 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. And individual neighborhoods are super walkable. 

As far as cars go, Chicago is pretty driveable. But I don’t really recommend getting a rental car if you’re only visiting. It just doesn’t make much sense. But if you insist, use Discover Cars. I also have a guide on driving in Chicago, which includes local rules and tips.

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 – Group Your Activities by Neighborhood

The activities in this itinerary are specifically organized by location, to keep you from unnecessarily hopping all over the city and spending too much time in transit. If you decide to branch out from this itinerary and do your own thing, just be sure to plan things by neighborhood, to keep things simple. 

For example, don’t plan to go to Lincoln Park, then the Museum of Science and Industry, and then back to Downtown Chicago. You’ll waste a lot of time. Instead, group things together by neighborhood. 

Tip #3 – Always make reservations if possible

Chicago restaurants, especially the popular ones, book up fast. 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 #4 – Let’s Get Real About Chicago Safety

Listen, I get it. Chicago doesn’t exactly have the nicest reputation when it comes to safety. But take it from someone who lives here: you’ll be ok. 

Remember, Chicago is a massive place. The city absolutely has pockets that are seedier than others. And wandering downtown alone at night isn’t something I’d do as a woman. Neither is taking the train at night. But these are also things I’d avoid in other major cities. So, just follow common sense. 

But if it’s daytime, or you’re with a group, you’ll be just fine doing most things on a visitor’s itinerary, including everything on this one. Just be mindful of your surroundings and listen to your gut.

The one tip I will give is to avoid talking to homeless people or making eye contact on the train. The harsh reality is that many of these individuals have mental health or substance abuse issues. If they ask for money (common), politely decline and say you don’t have any cash. It’s better to be safe than sorry. 

For more, read my full Chicago safety guide here. 

Tip #5 – Consider a Chicago CityPASS

To save some money, consider purchasing a Chicago CityPASS. For a fixed price of $144 for those 12+ and $114 for children ages 3-11, you’ll get access to five attractions, including the 360 Observation Deck, an architecture river cruise, and other attractions included in this itinerary.

Tip #6 – 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. Then, you can just tap your phone when getting on a bus or taking the train.

Tip #7 – 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 to do Chicago on a budget

FAQs

How many days do you need in Chicago?

3-5 days is enough time to visit Chicago. For seeing the top tourist attractions and exploring some different areas, 3 days in Chicago is enough, just know your days will be packed. If you want a slightly slower-paced trip, 5 days will provide extra leisure time. 

When is the best time to visit Chicago?

Spring through fall is the best time to visit Chicago. Specifically, the months of April through October. Read our guide for more information on the best time to visit Chicago.

Is visiting Chicago worth it?

Visiting Chicago is absolutely worth it! I can’t say enough good things about this city. Chicago has awesome attractions, trendy and unique shopping, some of the best restaurants, amazing neighborhoods, and so much more. It’s also just a beautiful cityscape with gorgeous Lake Michigan scenery.

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That’s it for this itinerary! Whatever you do, you’re sure to have a blast. For more Midwest fun, check out my list of day trips from Chicago.