Chicago itinerary – 3 days in Chicago for first timers

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

Published: July 18, 2024
Chicago

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

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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)

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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)

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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

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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!)

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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
Go City Travel Expert

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Male lion at Lincoln Park Zoo in Chicago
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Lincoln Park Zoo vs. Brookfield Zoo Comparison of Chicago Zoos

Love animals? Well, of course you do! After all, you’re not some sort of monster, right? Right? Why else would you have landed up on a blog comparing two of Chicago’s best animal attractions? Unless, of course, you’re planning some sort of Madagascar-style breakout. In which case, there’s nothing to see here. Move along, you’ve come to the wrong place. For the rest of you – lovers of adorable aardvarks, cute crocs and bewitching bears – we have exactly what you’re looking for. Take a walk on the wild side with us as we take a look at what to expect from Chicago’s Brookfield and Lincoln Park Zoos… Lincoln Park Zoo Name. This one’s fairly self-explanatory: it’s named after the President-referencing Chicago park in which it’s located, a huge tract of parkland on the shores of Lake Michigan that’s also home to a nature museum, a history museum and a conservatory. Age. Lincoln Park Zoo was established in 1868, making it one of the oldest zoos in North America. What to expect at Lincoln Park Zoo. At the risk of stating the obvious, Lincoln Park Zoo is perhaps best known for its animals. Many animals. Big animals. Little animals. Hairy animals. Scaly animals. Animals of all stripes, in other words. We’re talking over 1,000 critters across 200 species, including critically endangered eastern black rhinoceroses, dangerously cute American black bears, lovable two-tailed sloths, ultra-rare Jamaican iguanas, and a chimp named Optimus Prime, to name just a few. Lincoln Park zoo is also an accredited arboretum, boasting 850 plant species, including the only perennial herbaceous hibiscus collection in the United States. There are multiple exhibits to explore and regular activities like penguin-feeding, polar bear care and giraffe training. Best of all, it's free. That’s right: entry to Lincoln Park Zoo costs nothing. It’s free, it’s gratis, and it won’t cost you a dime! Getting in. Opening hours are generally 10AM-5PM with late opening until 7PM on weekends. The zoo is open 365 days a year and… entry is always freeee! More info here. Vital Statistics Size. A relatively diminutive 35 acres. Number of animals. Around 1,100 animals representing 200 species. Number of exhibits. There are around 15 exhibits, including an Arctic tundra for the polar bears, a macaque forest, a seal pool, a reptile enclosure and a petting zoo. Places to eat and drink. Four. Annual visitors. Around 3.4 million. Why Choose Lincoln Park Zoo? It's centrally located, just 20 minutes north of downtown. Its relatively small size means you can combine a trip here with other nearby attractions – among them the beautiful Lincoln Park Conservatory and North Avenue Beach. Penguin feeding! Giraffe training! Cute miniature train! Endangered species carousel! It’s one of few places on the planet you can encounter critically endangered eastern black rhinoceroses and the stately Jamaican iguana, believed to be extinct in the wild. Did we mention it’s FREE? Brookfield Zoo Name. Brookfield Zoo Chicago (to give it its full Sunday name) is also known as the Chicago Zoological Park. Or just plain Brookfield Zoo to its friends. Age. Brookfield Zoo is officially a nonagenarian: it first opened its gates on July 1, 1934. What to expect at Brookfield Zoo. One thing’s for sure: you’ll do a lot more walking at Brookfield, so wear comfortable shoes and bring plenty of water and snacks. Located out in the ‘burbs west of the city, this huge expanse of parkland is home to thousands of animals, from cute and cuddly koalas to showboating frilled lizards, Andean cock-of-the-rocks, and colorful butterflies. Say g’day to wombats, kangas, kookaburras and other Antipodean animals in the Australia zone, get up close to endangered black rhinos at the pachyderm exhibit and ogle Day-Glo pythons and poison frogs in the reptile enclosure. The zoo also has several fairground-style rides including a Ferris wheel, a hand-carved menagerie carousel, and virtual reality wildlife experiences. You can also rest weary legs aboard the motor safari and enjoy various up close encounters with animals (playtime with the macaws, shark-feeding and so on). Extra charges apply for all rides and animal encounters. Getting in. The zoo is open 9.3AM to 6PM daily. You can buy tickets for general admission, plus parking, special events and rides, here. Vital Statistics Size. At a whopping 235 acres, it’s somewhat larger than Lincoln Park Zoo.  Number of animals. Unsurprisingly, a space this size also houses more critters. About three times the number, in fact, at 3,500 animals and more than 500 species.  Number of exhibits. Eighteen zones, including wolves in the woods, a seasonal butterfly enclosure, a rainforest where clouded leopards are stars of the show, and a penguin pool. Places to eat and drink. Twelve: everything from burgers and tacos to gourmet popcorn and snow cones. Annual visitors. Around 2.2 million. Why Choose Brookfield Zoo? Despite its suburban location, Brookfield Zoo is a fairly easy 20-30-minute drive from downtown Chicago. With more than 3,500 critters to meet, plus rides, add-on experiences and more, there’s plenty to keep kids and grown-ups entertained here for a whole day – or longer! Cute koalas! Beautiful butterflies! Immersive virtual reality wildlife experiences! A Ferris wheel! Multiple restaurants and snack bars mean even the most bear-like appetites can be satisfied with ease. Save on Chicago Tours, Activities and Attractions Did you know you can save up to 50% on dozens of bucket-list Chicago tours, activities and attractions with a pass from Go City? Well, now you do! Choose from an Explorer or All-Inclusive pass depending on your sightseeing style and unlock access to the 360 Chicago observation deck, Navy Pier Ferris wheel and rides, Shedd Aquarium, Field Museum and many more. Find out more about the Explorer and All-Inclusive options and bag your Go Chicago pass here!
Stuart Bak
Stuart Bak
A walker takes in Chicago's fall color
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Chicago in November

Visit Chicago in November and you’ll discover a city preparing itself for the depths of winter but not quite done with fall. Temperatures are generally healthy enough to allow you to still spend plenty of time outdoors, where it’s usually possible to see the last of the fall color or the first flurries of snow. As the days get shorter towards the end of November, there’s also the start of the Christmas festivities to look forward to as well as the celebrations around Thanksgiving on the fourth Thursday of the month. Wondering how cold Chicago is in November and what there is to do? We’ve brought together all the top tips so you need to look nowhere else. Enjoy the end of the fall color Chicago weather in November sees average daily temperatures rise to 50°F, equivalent to a cool spring day. Whilst you’ll want to wrap up warm, do so properly and just eight days of rain will mean you can get out amidst the city’s green spaces to take in the final days of reds, oranges and gold with the turning of its leaves. Should you choose, you could traverse Chicago’s shores on Lake Michigan without ever leaving parkland. A popular pick with those looking to get into the saddle of the city’s rental bicycles – but welcoming to walkers, joggers and skateboarders too – the Lakeshore Trail covers 18.5 miles. Starting at Edgewater Beach in the northern suburbs, it then runs south past many of the city’s top attractions. The first is the free-to-visit Lincoln Park Zoo, whose residents include great apes, big cats, a burr oak older than the city and the Lionel Train Adventure and Endangered Species Carousel rides. Further south lie other major things to do in Chicago in November including the magnificent Field Museum. As one of the largest natural history museums around, it is simply stuffed full of stuffed animals, cultural artifacts from across the globe and the famous skeleton of Sue the T-Rex – one of the most complete and best-preserved examples yet discovered. A short way across the state border, alternative vistas can be sought out at Indiana Dunes National Park. Situated close to the southernmost point of Lake Michigan, the park’s impressive dunes offer a wealth of walking trails, albeit without the fall color. Kick off the festive season Thanksgiving focusses very strongly on Chicago’s downtown areas. Taking place on the grid of streets which form immediately south of the fork in the Chicago River, the annual Thanksgiving Parade is a family-friendly affair which sees State Street taken over by giant helium balloons, dance troops and marching bands. Thanksgiving is also closely associated with the Black Friday sales. Still on State Street, there are a great number of smaller stores, whilst the Magnificent Mile boasts higher end boutiques, department stores including Marshalls and Nordstrom and several shopping malls. If you prefer the artisan touch, look no further than the Chirstkindlmarket that appears in front of Daley Plaza’s 50-foot tall steel Picasso sculpture towards the middle of the month. Its German-style wooden chalet-like stalls are awash with beautiful ornaments, jewelry and tasty treats. Alternatively, you might want to try your hand at another winter staple – ice skating. The city’s largest outdoor rink is the McCormick Tribune Ice Rink that sits beneath the gaze of Anish Kapoor’s Bean, although the Maggie Daley Park Skating Ribbon provides an attraction that’s a little more unusual, with a track winding through the tree cover twice the length of a lap around the Bean’s rink. Savor the views With such a long list of things to do in Chicago in November you shouldn’t forget to stop for a moment or two and take in the windy city in all its glory. One way to do this would be to give your feet a rest by opting for the Hop-On Hop-Off sightseeing bus instead. Taking in sights you might otherwise miss, it also connects up many of Chicago’s top attractions, including the Willis (Sears) Tower. Entering the history books as the world’s tallest building from its topping out ceremony in 1974 until 1998, it continues to host the highest observation tower in the United States – the Skydeck. From its 103rd floor vantage, visitors are able to take in no less than four states whilst feeling the building move in the wind at almost 1400 feet up. Giving the Willis Tower a good run for its money is 360 CHICAGO at 875 North Michigan Avenue. Although its views come from nine stories below the Skydeck, its wrap-around glass windows still have extraordinary panoramas over the city. Get better acquainted with the city’s art Art lovers don’t need to look far in Chicago in November to get a fill of their passion. For one, the city has a huge array of public artworks. As well as the giant sculpture by Picasso in Daley Plaza and Anish Kapoor’s Bean, Chicago also has outdoor works by Joan Miro, Marc Chagall and Magdalena Abakanowicz. The immense Merchandise Mart building comes to life with the world’s largest video installation, projected annually onto the side of the structure from September through November. There’s also an impressive array of murals covering the ends of buildings throughout the city. West Town Street has developed into a mile-long open-air gallery, with other works including the mural of local photographer Vivian Maier in Wicker Park and an unforgettably bright 100 foot image of American singer-songwriter Muddy Waters on North State Street. The pick of the galleries includes the Art Institute of Chicago. One of the largest museums of its kind, the 300,000 objects in its permanent collection spans the genres, ranging from native American textiles to contemporary photography. Making the most of Chicago in November With so much to see and do in Chicago in November you won’t want to waste a second. Skip the lines and save big on admission to many of the city’s top attractions with Go City. Then the only thing left to do is have an incredible time in one of America’s greatest destinations!
Ian Packham

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