Chicago

Chicago itinerary – 3 days in Chicago for first timers

This popular Chicago itinerary includes the best things to do during your three days in the Windy City!
By Katie Sagal

Chicago offers diverse cultural experiences, world-class museums, exciting culinary adventures, and renowned architecture.

We just made your trip a lot easier with our 3 Days in Chicago itinerary. From arts and culture to science and entertainment, you’ll find a little bit of everything on this itinerary. As Chicago weather varies so dramatically between seasons, we've also included some indoor and outdoor options, so you can make this itinerary work for a vacation at any time of year.

This 3-day itinerary includes:

  • Big Bus Chicago Hop-On Hop-Off Bus Tour
  • Shedd Aquarium
  • The Field Museum
  • 360 CHICAGO
  • Magnificent Mile (free!)
  • Navy Pier Centennial Wheel & Rides
  • Skydeck Chicago
  • The Art Institute of Chicago
  • and more!

🗓️ >> Only have a few days in Chicago? We’ve also put together a 1 day and weekend in Chicago itinerary.

DAY 1 Stop #1: Hop-on Hop-off Big Bus Chicago tour

This is the perfect introduction to the Windy City. The Big Bus Chicago Hop-On Hop-Off Tour will take you past all the top attractions and landmarks, and your knowledgeable and friendly tour guides will fill you in on important facts and insider info. It’s a great way to get oriented within the city as a whole before you start exploring on your own.

A few of the highlights of your tour include the Museum Campus, Navy Pier, Water Tower Place Mall, Willis Tower (formerly Sears Tower), and more. You’ll be able to disembark at most landmarks, so it’s easy to use this to further your itinerary (traffic can be a factor, so don't rely exclusively on your Big Bus for transportation). Or, as the tour lasts two hours, you could stay on the bus for the whole route to see as much of the city as possible.

Getting In: Hop On Hop Off Chicago Bus Tour tickets are included on all Go City® Chicago passes.

Stop #2: Shedd Aquarium

shedd-aquarium-chicago

Next, head down to Chicago’s Museum Campus and pay a visit to its crown jewel – the Shedd Aquarium. Home to 32,000 fascinating and unique creatures from a range of diverse habitats, Shedd is one of the best aquariums in the country. Popular exhibits included with your admission are Waters of the World, Caribbean Reef, Amazon Rising, Abbott Oceanarium, Wild Reef, and the Polar Play Zone. Be sure to check out their new attraction, Underwater Beauty.

Shedd Aquarium also allows you to get up close with the animals – you can feed stingrays at "Stingray Touch" at no additional cost. However, if you want a truly memorable experience, you can meet a beluga whale, a sea otter, or a penguin, for an additional fee. Check out the Shedd Aquarium's Extraordinary Experiences for more information. We recommend reserving at least 2-3 hours for this attraction.

Getting In: Shedd Aquarium tickets are included on the Go City® All-Inclusive Chicago pass only.

Stop #3: The Field Museum

field-museum-chicago-brilliant-blue-sky

After lunch, head to this popular natural history museum for an educational and entertaining afternoon. The Field Museum has spent over 100 years curating and adding to its collections, so you know their selection and breadth of artifacts and objects will be impressive.

Some of the highlights of their collection include SUE, the famous T-Rex (the most complete skeleton of her species), the notorious Tsavo Lions, an extensive collection of Ancient Egyptian artifacts, a beautiful selection of gemstones and minerals, and the fun “Underground Adventure” exhibit. We recommend reserving between 1-2 hours for this attraction.

Getting In: The Field Museum tickets are included on the Go Chicago pass.

Stop #4: Adler Planetarium

adler-planetarium-located-downtown-chicago

End your day with a visit to the last (but by no means the least) of the Museum Campus institutions. The Adler Planetarium has a lot to offer curious visitors. With nine special exhibits, multiple theaters, and the historic Atwood Sphere experience, there are tons of fun activities that the whole family will enjoy.

Popular exhibits include Chicago's Night Sky, Planet Explorers, Imagine the Moon, Our Solar System, and more. This is a must-see attraction for any aspiring scientists or space lovers in the family. We recommend reserving about 1 hour for this attraction.

Getting In: Adler Planetarium tickets are included on all Go City® Chicago passes.

DAY 2 Stop #1: Chicago Theatre tour (indoor option)

chicago-theatre-lights-dusk

Take a tour of the iconic Chicago Theatre, home to legendary performances by world-class actors. One of the most well-regarded theaters in the country, the Chicago Theatre is a must-visit for history buffs and culture lovers.

On this tour, you’ll get to walk across a stage that’s played host to the likes of Frank Sinatra and Dean Martin and gaze at the French Baroque interiors. Plus, you'll see the walls with tons of celebrity autographs scrawled across them. This venue is a beauty from top to bottom.

Getting In: Chicago Theatre Tour tickets are included on all Go City® Chicago passes.

Stop #1: Architecture River Cruise (outdoor option)

Start off your morning with a beautiful cruise down the Chicago River. This cruise only runs during the warmer months (and can be a bit too chilly during the early spring and late fall, even if it is running), so we recommend reserving this attraction for the warmest times of the year. This insightful cruise will provide you with background information on Chicago’s most iconic landmarks and its famous skyline, practically building by building.

Some of the highlights you’ll see on your Architecture River Cruise include buildings by Mies van der Rohe, Skidmore Owings Merrill, and Helmut Jahn, plus the Willis Tower and the Old Post Office Building. It's a must not only for fans of architecture but for anyone who wants to get a feel for Chicago's history, particularly the history of the built environment after the Great Chicago Fire of 1871.

Getting In: Chicago Architecture Boat Tour tickets are included on the Go City® Chicago Explorer pass only.

Stop #2: 360 CHICAGO

360 Chicago

At the top of the iconic John Hancock Tower, you'll find the awesome 360 CHICAGO observation deck. From your 94th-floor vantage point (over 1000 feet in the air!) you’ll get unparalleled views of Lake Michigan and the city below, especially if you're daring enough to lean out on the tilted glass.

What's more, the elevator to the top is the fastest in the city, whizzing you from the ground to the observation deck in under a minute.

A visit here is both a great photo opportunity and a good chance to learn more about Chicago’s famous architecture. As a bonus, this attraction is very conveniently located in the heart of an area you'll want to explore anyway: Michigan Avenue. We recommend reserving at least 1 hour for this attraction.

Getting In: 360 CHICAGO tickets are included on all Go City® Chicago passes.

Magnificent Mile (free!)

magnificent-mile-sign-chicago

Once you leave 360 CHICAGO, wander along Michigan Avenue (aka. the Magnificent Mile) in search of some more fun. There's a boatload of shopping around, including everything from affordable fashion to high-end boutiques that are just perfect for window shopping. There are also endless dining choices, so you're sure to find something of interest down Michigan Avenue.

You’ll find plenty of options, especially if you explore side streets. The nearby Water Tower Place Mall has a food court, too, which offers a selection of options that even the pickiest eater will find delicious.

Stop #3: Chicago Children's Museum (indoor option)

Located right on Navy Pier, the Chicago Children’s Museum is a family favorite. Full of interactive exhibits, dynamic displays, and educational fun, there’s so much to do at this institution that your kids will never tire of it. Featured exhibits and areas include Dinosaur Expedition, where kids can explore a real excavation pit where dinosaur fossils were discovered, and Tinkering Lab, which allows kids to exercise their creativity and analytical skills by playing around with different parts and tools.

Getting In: Chicago Children’s Museum tickets are included on all Go City® Chicago passes.

Stop #3: Bike rental (outdoor option)

riding-bike-hands-free-park

After lunch, head down to the Navy Pier area to get a little exercise. Rent a bike and enjoy the waterfront on two wheels! Chicago is a cyclist’s paradise, filled with trails, parks, and pathways just waiting to be explored.

There are 26 miles of lakefront trails for you to enjoy, so you’ll really be able to get a feel for the beautiful scenery. Your rental is valid for 4 hours, but if you want to see an additional attraction today we recommend reserving only 2 hours for this attraction.

Getting In: Bike and Roll Chicago rentals at Navy Pier are included on all Go City® Chicago passes.

Stop #4: Navy Pier Centennial Wheel

time-photo-navy-pier-centennial-wheel

Whether you've tootled around on a bike or explored the Children's Museum, be sure to also reserve some time to explore the Pier itself. It’s Chicago’s most-visited free attraction and has tons to offer the out-of-town visitor. With attractions as varied as the Chicago Children’s Museum and the Chicago Shakespeare Theater to a massive concert venue, you can practically spend the entire day here!

One of the most popular attractions on Navy Pier is its iconic Ferris wheel, visible from many vantage points across the city. There are also a few other theme park-style rides to enjoy, from swings to a mini-golf course. Although entrance to the Pier itself is free, your Go City® Chicago pass covers the admission costs for the Centennial Wheel and other rides. We recommend reserving 1 hour for this attraction.

Getting In: Navy Pier Centennial Wheel tickets are included on all Go City® Chicago passes.

DAY 3 Stop #1: SkyDeck Chicago

Skydeck Chicago view

Check out Chicago’s other sky-high attraction – SkyDeck Chicago at the Willis Tower. From the 103rd floor of the tower, you’ll be treated to stunning and unbeatable views –1,353 feet up in the air! Some of the highlights you’ll be able to see in the city below include everything from Navy Pier to Soldier Field and the Museum Campus. Don’t forget to bring your camera to this attraction! We recommend reserving 1 hour for this attraction.

Getting In: SkyDeck Chicago at Willis Tower tickets are included on all Go City® Chicago passes.

Stop #2: The Art Institute of Chicago

art-institute-chicago

Now’s the time to explore the artsy side of Chicago with a visit to one of the country’s most prestigious art museums. The Art Institute of Chicago features celebrated collections of modern and contemporary art, architecture, design, and photography, as well as Impressionist paintings, decorative arts, and more.

Some of the most famous pieces at the Art Institute include the Chagall stained glass windows, Grant Wood’s American Gothic, Matisse’s Bathers by a River, and Georgia O’Keeffe’s Black Cross, New Mexico. We recommend reserving at least 2 hours for this attraction, perhaps more if you’re an art lover.

 

Stop #3: Millennium Park (free!)

cloud-gate-bean-black-white

Take some time to stroll around this beautiful urban greenspace. Be sure to note highlights like the Pritzker Pavilion – an architectural marvel – and the charming Lurie Garden. You can also explore some of the park’s iconic works of art. Be sure to check out the Crown Fountain and the Cloud Gate sculpture (also known as the Bean, pictured above).

Get your cameras at the ready when you're at the Bean. It's one of Chicago's most recognizable spots and a go-to for a vacation snap! There will also be several special events going on in the park from late spring to early fall. Do a little research before your visit to see what's on. You can expect everything from prestigious concerts to food festivals and free yoga. We recommend reserving about 1 hour to explore the park; more if you're participating in an event.

Getting In: It's free to explore Millennium Park, but any additional activities may incur extra costs not covered by the pass.

Chicago has something for everyone

So, doesn’t that sound like the best three days in Chicago you could wish for? With a great mix of art, culture, entertainment, education, and just plain fun, we know this Chicago itinerary will please first-time visitors and returning customers alike.

Don't forget to make the most of your evenings in Chicago too. Check out our Chicago nightlife guide for some more fun ideas to add to your itinerary.

Save up to 50% on Chicago attractions  

Planning your Chicago trip? With Go City®, you can explore big-name landmarks, local hotspots, and epic tours, all on one pass, all for one price. Not only that, but you'll enjoy savings of up to 50%, compared to buying individual attraction tickets. So pick up your Chicago pass and get exploring! 

☀️See all Chicago attractions ☀️ – 🌏 Explore other destinations 🌏 – ✈️ Buy a Chicago pass ✈️ 

Katie Sagal

Continue reading

things to do in uptown chicago
Blog

Things to do in Uptown, Chicago

Heading to Chicago for your vacation? Why not check out Uptown? There's heaps of entertainment on offer, so make sure you see as much as possible! Here's our guide to all the best bits. Including Eastern delights Sun, sea, and sand Street Art A boozy visit Starlit shows and more! Argyle Street Let's start things off with a shopping extravaganza. Uptown's got some fantastic spots, but we want to focus on one that's rather unique. Head to Argyle Street, and you'll feel like you've been transported to a completely different place. But why is that? Well, it's because countless Vietnamese, Thai, and Cambodian businesses call it home. Colloquially referred to as 'little Vietnam', this pedestrian-friendly area has tons to see and do. Take a stroll and find plenty of unique produce to whip up your own Asian masterpieces, or simply buy it from the experts at many of the food stalls and restaurants. Looking for some interesting pieces for your home, or accessories to adorn your body? There are a wide variety of clothing, plant, and knickknack joints that'll tickle your fancy and then some. The beach Sometimes, we all need a little sun, sand, and sea in our lives. Nothing quite lifts the spirits than a trip to the beach, especially when the sun is sizzling in all its glory. Well, Uptown's got you covered, thanks to Montrose Beach. It's Chicago's biggest beach at over 56,000ft squared, and you'll find plenty of food, drink, and fun within a stone's throw of your bathing spot. Hire some equipment and enjoy some watersports, relax under the sun (and plenty of sunblock), or go take your dog for a walk in the pup-friendly area. Easily one of the best things to do in Uptown if the weather's good. Street Art If you're the kind of person who has their head turned by street art, you're in luck. Chicago is brimming with murals and pieces all over the city. And yes, while some are admittedly better than others, you don't even need to go looking. Instead, head to the Clifton Avenue Street Art Gallery, where you'll find a curated mix of pieces from all over the world, including some from Chicago natives. Ideal for those of you looking to increase your follower account. We know that's important to some of you. Distill Chicago-style Do you like spirits? Not ghosts, the other kind. The kind you sip with class, or slam down with reckless abandon. Yes? Yes, of course you do. Well, have you ever wondered where those spirits come from? Sure you have. If you want to see the process in action, especially for local craft brewers, head to Koval Distillery in Uptown. See how this local husband-and-wide duo, who've been crafting their own take on spiritual classics for nearly 15 years. You'll see how they've upped their production to serve a long list of customers both in Chicago and further afield, and how they've grown to accommodate gin, whiskey, and other liqueurs. Go tour the premises, pick up some for yourself, or stick around for a cocktail class. Nights out with style If you're looking for a fun night out, Uptown has a lot on offer. There's tons of places to wet your whistle, but why not combine your night out with some great live music? Carol's Pub is half a century old, and still going strong. It's a no-nonsense place where you grab a beer and a bite, or sample the revamped cocktail menu. However, every weekend they have three days of live music, with bands playing on Friday and Saturday, and a karaoke night on Sunday to help you end the week on a high before the Monday blues creep in. Or, for a bit more of an upmarket vibe, check our Green Mill Cocktail Lounge. For over a century, it's been the city's go-to place for the Chicago jazz scene. Even infamous Chi-Town gangster Al Capone frequented it back in the dark Prohibition days. You can even grab his booth, if you're lucky. Inside, you'll sip fine cocktails and nod your head to a wide variety of live performers in the jazz community. They even host slam poetry nights, if that's your scene. Looking for more modern music? Check out Riviera Theatre, an old cinema that now showcases an eclectic mix of indie rock, rap, and DIY punk acts throughout the year. Plenty of up-and-coming Chicago acts take the stage every week, so if you're looking for your next favorite song, head down and see what's cracking. Whichever place you choose, your night out will be one of the best things to do in Uptown when you visit Chicago! Catch a show or two Looking for a spicier night out? Don't you worry, dear reader. We've got some spicy samples that are guaranteed to hit the spot. Having recently moved across town from River North, the Baton Show Lounge now calls Uptown home. This hyped spot has hosted some of the biggest drag acts around, including Ru Paul and Madonna, among a long list of luminaries. Every night, you'll find a different act taking to the stage, giving it their all, and getting the crowd involved. Or, for a more varied cast of acts, check out Kiss Kiss Cabaret. Every week, you'll find a great burlesque, vaudeville, or magic show unfurling before your very eyes. Grab a drink, take a seat, end drink it all in. Pay your respects And finally, let's end this list with one of Uptown's most beautiful places. Graceland Cemetery might sound slightly morbid, but it's anything but. For approaching 200 years, it's been the final resting place of many of Chicago's most notable residents through time. Take a stroll and see if you can find the tomb of William Hulbert, who helped create the baseball National League, or famed film critic Roger Ebert. Alongside this monument to Chicagoans, you'll find plenty of trees and green space where you can go and relax after a long day, or bring a picnic during your vacation. A must-visit, and easily one of the best things to do in Uptown when you visit Chicago. And that's our list of the best things to do in Uptown, Chicago!
Dom Bewley
pilsen chicago
Blog

Things to do in Pilsen, Chicago

Do you like your neighborhoods to have the perfect mix of cool, community, and culture? Then give Pilsen a go! This district of Chicago has some great and unique entertainment opportunities for travelers and locals alike. So, if you're visiting Chi-Town on vacation, these are the best things to do in Pilsen! Including Live music BBQ with a glamorous twist Some culture Parks Street art and more! Get live We begin today with music. Live music, to be exact! Nothing quite beats seeing a band jam in the flesh, and lucky for you, Pilsen has a few awesome venues to check out. One of Pilsen's oldest landmarks is Thalia Hall, which is over 120 years old and still going strong! This powerhouse of live entertainment hosts comedy greats like Dave Chappelle as well as huge bands like The Smashing Pumpkins, among many others. In recent years, the addition of several bars, restaurants, and alternative stages have grown Thalia Hall's entertainment opportunities. So go check out what's on when you're visiting Chicago. If you prefer your music noisier, your performance wilder, and your gigs more carefree, then check out The Dojo. Chicago's premier underground music venue hosts local noise bands, leftfield artists, and much more. Every weekend they have new and exciting alternative acts gracing the stage, so head down there and see what all the fuss is about! Carnival BBQ BBQ is the backbone of America. For decades, we've ventured out of our abodes, fired up the grill, and invited friends and family over for a cookout. Nothing brings the community together better than BBQ. And Pilsen has a quality BBQ joint with a musical twist. We're talking about Honkey Tonk BBQ, where hungry souls can go to fill their bellies and their minds, thanks to the jazz and blues parties they host most nights. Chow down on some delicious BBQ meat, and then work off the calories through the night. But one Saturday a month, they mix things up a bit, as the place is taken over by an improv burlesque quintet. They'll have you dancing and laughing in no time. Easily one of the best things to do in Pilsen when you visit Chicago! Get cultural Next, let's switch gears to something more cultural. If you're looking for some inspirational, mind-opening experiences, then Pilsen's got you covered. At the National Museum of Mexican Art, you'll find art from Mexicans both in the US and across the border. Chicago is known as the 'Mexico of the Midwest', and this museum is a testament to the artistry of many Mexicans who now call Chi-Town home. Wander through over 7000 pieces, and learn about the stories that helped create them. Or, if your tastes lie a little leftfield and you want something exclusive, then House of the Apocalypse might be just what you're looking for. Only open for four hours every month, this weird and wonderful collection of artwork is quite the sight. Featuring sci-fi and post-apocalypse influences, House of Apocalypse's collection is something you won't quite find anywhere else. Street art named desire If you prefer your artwork of the outdoor, urban variety, or simply want to peruse in the glow of the sun, then go check out the massive collection of street art on 16th Street. Brought together thanks to a collaboration between multiple local institutions, you'll find a wealth of works from global street artists. In fact, this collaboration has helped restore a lot of the area, which was once derelict and dirty. So, two birds with one stone then! At the same time, it's ensured that Pilsen remains true to its roots, and doesn't sway too far into the gentrification we've seen happening all over America and other parts of the world. Pilsen is community-first, and always should be. More eateries! And when all that activity brings on the hunger prangs, Pilsen's got some great restaurants to sate your grumbling tummy. Head to Barrio for some authentic Mexican cuisine and a whole menu dedicated to tequila-based cocktails! What some fresh, farm-to-table dishes at a reasonable price? Go check out Dusek's Tavern. Their fixed menu of exciting, New-American cuisine means you get delicious food and a great price. In the market for some delicious East-Asian delights? Give HaiSous Vietnamese Kitchen a look. With a mix of street food, fixed dishes, unique family recipes, and a fine line of cocktails to boot, it's a must-visit for anyone visiting Pilsen. Drinks After all of those activities and food, the next stop on your Pilsen journey should be one of its many watering holes. Thankfully, Pilsen is full of them, so you have the pick of the litter. Want some classic pub food, refreshing craft beer, and cool aesthetic on your night out? Skylark's the one. Want to try something a little kookier? How does a hidden basement bar with creative punches sound? That's Punch House, which has a whole menu full of fruity punches to try, as well as sandwiches, all rolled into a retro-vintage vibe. Doesn't get more Pilsen than that! Or, grab a slice of pizza and pick from any number of craft beers at The Green Room Tap. Whichever way you decide to go, you're bound to have a blast! Find a park-ing spot Let's end this list on a walk through some of Chicago's green and pleasant land. Of course, we're talking about parks. And, of course, Pilsen's got its share of great ones! Firstly, there's Harrison Park, which has a gym, indoor pool, and even meeting rooms housed within the Fieldhouse. So, if you like to get active, you can do it inside or out. Beyond that, you'll find over 18 acres of sweet green space to go sit, have a jog, or prepare a picnic. Look out of the bust of Emiliano Zapata, one of the biggest names of the Mexican Revolution. Or, check out Dvorak Park, which boasts a baseball field, its own pool and unique water feature, soccer pitches, playgrounds, and a whole heap of comfortable, welcoming grass. You may even catch the odd performance there on the right day, as there's a big art scene that calls the park home. The playground is perfect for kids, if you're bringing the little ones. And that's our list of the best things to do in Pilsen, Chicago!
Dom Bewley
chicago-illinois-usa-on-lake-michigan
Blog

Things To Do in Chicago When it's Hot Out

Looking for ways to beat the heat in the Windy City? Even though Chicago's nickname implies that the breeze is always flowing, on a sweltering day that may not be the case. And while there are plenty of things to do in Chicago, when it gets this hot you might start to plan your day around where you'll find the most AC exposure. Luckily, Chicago is full of diverse attractions that will keep you busy on the hottest of days. Here are some of our favorite things to do in Chicago when it's hot out, including... Shedd Aquarium SkyDeck Chicago or 360 Chicago Shoreline Architecture River Cruise Art Institute of Chicago Adler Planetarium The Field Museum Chicago's Children Museum LEGOLAND Discovery Center The Escape Game Chicago Museum of Science and Industry Chicago Children's Museum This is the perfect place to bring the kids when they've had enough of the heat. Located right on Navy Pier, the Chicago Children's Museum will keep everyone busy for hours. Each exhibit at the museum is aimed to teach children a different learning experience through interactive and fun displays. At Play it Safe, kids can explore a realistic firehouse. In the Tinkering Lab, they'll have the freedom to innovate and create with various different DIY projects. The kids will be entertained all day long and parents can sit back and enjoy the learning process. Getting in: Chicago Children's Museum tickets are included on Go Chicago Card. LEGOLAND Discovery Center Another great place to go with the family is the LEGOLAND® Discovery Center. This massive indoor space is filled with LEGO®-themed exhibits, construction demonstrations, interactive areas, and exciting attractions. Kids of all ages can enjoy the different activities and demonstrations that take place throughout the day. They'll learn the best LEGO® building secrets from Master Model Builders, become part of the LEGO® story at the 4D Cinema, and can save the princess on the Kingdom Quest Laser Ride. LEGO® lovers will cherish their time spent here as they learn and build firsthand. Getting in: LEGOLAND® Discovery Center tickets are included on Go Chicago Card. The Escape Game Chicago Can you escape? Test your skills, grit, smarts, and ability and see if you have what it takes at The Escape Game Chicago. An escape room is the perfect place to go on a day when the heat is just unbearable. At Escape Game Chicago, you'll have your choice between four different themed escape scenarios. Choose from Mission Mars, Gold Rush, Prison Break or The Heist. You'll race against the clock during each of them to escape! While children are allowed to participate in The Escape Game Chicago, it is recommended for players age 13 and up as some of the content may be too difficult for younger children to understand. Getting in: The Escape Game Chicago tickets are included on Go Chicago Card. More Chicago Attractions There’s no shortage of things to do in Chicago when it’s hot out, and the suggestions above are just some of our favorite indoor activities. We hope you'll add a few to your Chicago to-do list. Check out a Go Chicago Card to see all 28 Chicago attractions, and see what you can do this summer in Chicago!
Nicole Muto

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.

Thick check Icon