A week in Chicago for first timers

It’s an expansive urban setting, with many diverse neighborhoods that all have unique offerings in the way of sightseeing and attractions. While it’s simply not possible to visit each and every neighborhood, we’ve put together a list of the major areas of Chicago that you shouldn’t miss on your trip.

Published: July 18, 2024
Skyline Chicago

You can visit some, or all of these neighborhoods as part of a week-long vacation in Chicago. This list of suggested areas also includes our favorite attractions to explore, including world-class museums, popular tours and cruises, an amusement park, a zoo, and many more.

This itinerary includes popular attractions grouped by neighborhood or type of activity, including:

Magnificent Mile / River North: Big Bus Chicago Hop-on Hop-off Tour, 360 CHICAGO, Mag Mile shopping
The Loop: Art Institute of Chicago, Skydeck Chicago, Millennium Park
Museum Campus: The Field Museum, Shedd Aquarium, Adler Planetarium
South Lake Shore / Hyde Park: Museum of Science & Industry, Robie House, University of Chicago museums
Lincoln Park: Lincoln Park Zoo & Rides, Chicago History Museum
Navy Pier: Navy Pier Centennial Wheel and Rides, Architecture River Cruise, Classic Lake Tour

Spending less time in Chicago but still want to see the best of the city?

Check out our 1 Day2 Days/Weekend Getaway, and 3 Days in Chicago Itinerary.

Magnificent Mile / River North

Big Bus Chicago Hop-on Hop-off Tour

First-time visitors to the city, or those who haven’t been able to see and do a lot on previous visits, should take advantage of the opportunity to take a bus tour. Choose this hop-on hop-off option for maximum flexibility and fun.

They’ll narrate your progress as you go along in a fun and informative way, and you can get off at anything that interests you. Win-win! It also picks up conveniently at the Hancock Tower, which is great for travelers who want to see 360 CHICAGO, Water Tower Place Shopping, and other Mag Mile attractions.

360 CHICAGO

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360 CHICAGO makes for another perfect introduction to the city – from a totally awesome perspective! See the city from some 94 floors above ground level, and snap some amazing photos. There are also some fun exhibits to explore at the top, explaining the tower's background, the history of the city, and important events.

This observation deck is located in the Hancock Tower, conveniently right in the middle of the Magnificent Mile attractions.

Mag Mile shopping

Mag Mile

Along with Oak Street, Michigan Avenue is one of the shopping hotspots in the city. While shops do tend towards the high end, you’ll also find fast fashion and more affordable fare like H&M, Target, and UNIQLO. There are so many fun places just to window shop. If you’re visiting in December, be sure to keep an eye out for creative holiday window decorations. 

Getting In: It’s free to stroll Michigan Avenue.

The Loop Attractions

Art Institute of Chicago

One of the best art museums in the entire world, the Art Institute of Chicago should definitely be on your list. Their collections are impressively diverse, so even if you’re an accomplished museum-goer, you’re sure to find something new to enjoy at the Art Institute. You'll see everyone from classical Greek statuary to ancient Asian jewelry and modern painting. Plus, they have some awesome gift shops, so souvenir shopping = solved.

Skydeck Chicago

Skydeck Chicago

Another option for seeing the city from a bird's perspective is Skydeck Chicago. Located in the Willis Tower (formerly the Sears Tower), this fantastic observation deck provides unparalleled views of the city below. From your perch 103 stories in the air, you’ll see everything from Navy Pier down to Soldier Field. The Skydeck Chicago also features several interactive exhibits and displays, so you can learn about the history of the city and the building itself.

Millennium Park

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In this part of the city, you simply can’t pass up the opportunity to explore Millennium Park a little bit. This expansive greenspace is one of the modern marvels of the city, and plays host to a growing host of activities year-round, from yoga in the park to free concerts. Come here for fun free activities, and be sure to check out the public art, like “Cloud Gate,” aka, The Bean.

Museum Campus

The Field Museum

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On another day of your Chicago vacation, you’ll want to head down to the Museum Campus. This fantastic area of the city boasts three top museums, all of them must-visits. The Field Museum is one of the world’s leading natural history museums, offering exhibits of artifacts from millennia of world history. You’ll find all the most important natural artifacts, from precious gemstones to dinosaur fossils to ancient Chinese art and architecture. For those of you who have visited before, keep an eye out for SUE the T. Rex.

Shedd Aquarium

Shedd Aquarium

shedd-aquarium-chicago

Come here to see an amazing collection of aquatic critters, big and small. In fact, you’ll be able to see about 32,000 of them! You can explore diverse marine and freshwater habitats and learn all about their fascinating inhabitants. Featured exhibits include “Waters of the World,” “Amazon Rising,” and the “Polar Play Zone.”

Bonus: Go City® Chicago pass holders get priority entry! This can save loads of time during the busy summer months.

Adler Planetarium

adler-planetarium-located-downtown-chicago

Opt for all-access admission to the Adler Planetarium on your visit and you’ll get to see exhibits that study all facets of space, both known and unknown. A fun exhibit is the sky show “Planet Nine,” which focuses on the search for the new ninth planet. You should also check out the Historic Atwood Sphere – Chicago’s oldest planetarium! Adler even hosts frequent monthly “Adler After Dark” events which can be fun, too.

South Lake Shore / Hyde Park

Museum of Science & Industry

Voted one of the top 25 museums in a recent TripAdvisor poll, the Museum of Science and Industry in Chicago is a must-visit for fans of science and engineering. Here you can explore over 14 acres of exhibits and interactive displays at the largest (and arguably the coolest) science museum in the country. Featured exhibits include an indoor tornado, a real WWII submarine, an Illinois coal mine, and a mirror maze.

Robie House

Robie House

Located on the campus of the University of Chicago, this is one of the few Frank Lloyd Wright buildings in the area open for touring. Built for Frederick C. Robie in the early years of the twentieth century, this beautiful home is an excellent example of Prairie-style architecture. There are only a few FLW buildings in the world, so don’t miss the chance to see one of them up close.

Smart Museum of Art, University of Chicago

For another museum option in the area, head to the small but fantastic Smart Museum of Art. It’s an art museum affiliated with the University of Chicago, and it’s filled with rotating exhibits on a variety of artistic and cultural topics. You should also stop by the outdoor sculpture garden, which is a nice place for fun photos.

Lincoln Park

Lincoln Park Zoo & Rides

Lincoln Park Zoo

If you’re in the Lincoln Park neighborhood, then a visit to the zoo is in order. Come here to see a nice selection of your favorite animals in recreated natural environments, from grand polar bears to tiny turtles. The kids can also enjoy a few rides aboard the historical carousel and the Lionel Train Adventure.

Chicago History Museum

The Chicago History Museum is one of the city’s best resources for learning about Chicago history and culture. Even natives love to come here and explore their impressive collection of objects and artifacts that tell the important cultural history of their city. Definitely spend an hour or two here with the kids exploring exhibits like “Chicago Authored” and “Imagining Chicago.”

Navy Pier

Navy Pier Centennial Wheel and Rides

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Navy Pier is a major cultural destination in Chicago and everyone should spend some time there. Come here for the rides, the entertainment, the cruises, the bike rentals, and more. Visit the Children’s Museum (also on the Go Chicago Card). Take in a play at the exciting Chicago Shakespeare Theater space. Then hop aboard the Centennial Wheel!

Architecture River Cruise

An excellent way to learn more about the city and enjoy a relaxing hour on the water is to take the famous Architecture River Cruise, which departs from Navy Pier. This informative cruise will tell you all about Chicago’s famous architectural history, and point out the major buildings by the most renowned architects. Plus, you’ll get some killer pictures out of it!

Classic Lake Tour

Lake Michigan

Another cruise option for the Navy Pier area is the Classic Lake Tour. This 45-minute excursion takes you out onto Lake Michigan – a lake so big it has massive tides and many popular beaches – to see the city skyline from afar. As you sail along, you’ll be treated to professional narration about the city’s heritage and history.

Let’s Recap

This week in Chicago itinerary is designed to be a great introduction to the city, from top to bottom. It’s the perfect way to truly feel as though you’ve gotten to know the fantastic Windy City. Choose from any of these top attractions to craft your perfect week in Chicago! 

Save up to 50% on Chicago attractions with Go City®

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.  

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

Katie Sagal
Go City Travel Expert

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Fun Facts About Chicago: Your Essential Trivia

How much do you know about Chicago? Test your knowledge of the Windy City with our trivia below. These fun facts are sure to come in handy on your Chicago vacation! Top Chicago facts 1-10 The world’s very first skyscraper was erected in the city in 1885. Skydeck Chicago is a film star! Catch a glimpse of the experience in Ferris Bueller’s Day Off. The Willis Tower is the eighth tallest building in the world, coming in at 1,450 feet and 110 stories tall. Chicago invented deep-dish pizza. The Navy Pier Centennial Wheel was preceded by an iconic Ferris wheel, which welcomed over 17 million riders in its ten-year life span. Historic Route 66 begins in Chicago (and terminates in Santa Monica, CA). The Field Museum’s newest addition is Máximo the Titanosaur: the largest dinosaur ever discovered, weighing 70 tons. Chicago is known as “The Windy City” for the bombast of its politicians—not for its weather. Chicago is home to an impressive 56 museums, including the famous Art Institute of Chicago. The Taste of Chicago — a summer legend in Chicago — is the world’s largest free outdoor food festival. Top Chicago facts 11-20 The Museum of Contemporary Art is the only museum in the city to feature dozens of works with the title, “Untitled.” Batman’s iconic Gotham City was based on Chicago; not, as many people assume, NYC. The Lincoln Park Zoo is one of the world’s rare free zoos. Malört, one of the most distinctive liquors in the world (and some say the most unpalatable), was created in Chicago. Today, more than 90% of the national consumption of Malört is still confined to the greater Chicago area. The Adler Planetarium was America’s first planetarium. The Adler Planetarium is also one of the best places to get a great view of the skyline. The Museum of Science and Industry is one of the largest science museums in the world, with more than 400,000 square feet of exhibit space. The renowned Pablo Picasso sculpture, created specifically for the city and located in Richard J. Daley Plaza, weighs an intimidating 162 tons. It is also called 'Untitled'. Chicago's Brookfield Zoo was the first such institution in the world to successfully perform brain surgery on a gorilla. The Brookfield Zoo is also known for its majestic fountain, named for Theodore Roosevelt, the 26th President of the United States who is remembered for expanding protections on wildlife. Top Chicago facts 21-25 The Chicago Theater's grand lobby is inspired by the Royal Chapel at Versailles. The Chicago Theater also boasts one of the oldest Wurlitzer pipe organs remaining in existence. The Ernest Hemingway Home was the first house to have electricity in Oak Park. The American Writer’s Museum is the only museum in the world devoted exclusively to American writers and their works. The Shedd Aquarium has more than 32,000 animal inhabitants. Save on attractions Admission to many popular Chicago attractions is included with a pass for Chicago with Go City®. You could make big savings vs paying at the gate. Share your trip with us Follow us on Facebook and Instagram, and share your adventure with us. Tag us at @GoCity and use #GoCityPass on your travel photos to keep us up to date with your vacation!
Katie Sagal
A Chicago store and window display
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Best Chicago Souvenirs

Taking a trip to Chicago soon? It’s likely you’ll want to take something back home with you that reminds you of your trip. It’s equally likely you’ll want to buy a small item for friends and family you left behind. If you want to find souvenirs made in Chicago rather than tacky plastic items that have no real link with the city, you’ve come to the right place. We’ve got some fantastic ideas for the best Chicago souvenirs below! Edible Chicago souvenirs The main problem with edible gifts from the windy city is having the willpower to avoid consuming them all before you’ve even left downtown. Don’t be put off by the long lines which often stretch down the street from the Garrett Popcorn shops on West Jackson Boulevard and Michigan Avenue. Dishing up their ‘Chicago Mix’, half cheese and half caramel, to the people of the city since 1949, they’re clearly doing something right. Small bags cost as little as $3, though the souvenir skyline tins make a great keepsake long after the popcorn itself is all gone. They also have outlets at O’Hare Airport. With a pedigree dating back even further is Fannie Mae chocolates, which have been Chicago based since first opening in 1920. Head to one of their city center stores and you’ve got the option of creating your own mix of pixies, mint meltaways and vanilla buttercreams. At the upper end of the chocolate market is the Chicago-only Vosges Haut-Chocolat. With each chocolate hand-finished, the company is particularly well-known for their truffles, with flavors as diverse as hazelnut and balsamic vinegar and ginger with wasabi. As some indication of price, a box of 16 truffles will set you back around $50. On the savory front, The Spice House on North Wells Street in the Lincoln Park neighborhood (close to Chicago History Museum) offers more than the usual cooking herbs and spices. Their team has created a range of Chicago-themed blends that will brighten up your home cooking for weeks to come. Drinkable Chicago souvenirs The same can be said for another much-loved Wells Street store, Old Town Oil. Specializing in small-batch olive oils and vinegars from farms across the globe, they have some very tasty-looking gift boxes, and can even produce custom bottle labels. Oils and vinegars won’t quench your thirst, but beers will, with Goose Island an award-winning craft brewery set up to bring good beers to the Chicago streets. Using 15 different yeasts to turn the sugars into alcohol before aging the beer in bourbon barrels for extra flavor, visitors are welcome to the brewery tap room on Fulton Street or its Clybourn brewhouse to sample their selection of seasonal and year-round beers. With over 100 international prizes to its name, the Koval Distillery has come a hell of a long way since starting up in 2008 as the first new distillery in the city since the 1800s. Their copper vats produce whiskeys, gins and specialty spirits using organic grains. Everything from soaking of the grain to bottling takes place in house so the dedicated team are able to keep track of every step to produce their signature clean flavors. Jewelry and curios The Field Museum is another great place to keep a lookout for souvenirs. Its store is awash with goodies, though we’ve chosen to focus our attention on their jewelry selection. Linking back to the museum’s incredible natural history collection, it ranges from T-Rex earrings to necklaces and pendants threaded with natural stones such as quartz and onyx. Echoing the form of Chicago’s favorite piece of public art – Anish Kapoor’s Cloud Gate – Tiffany & Co’s Chicago store sells sterling silver bean pendants designed by Elsa Peretti. If the price tag stops you stepping beyond the window displays, various other outlets do similar pieces in base metals. But if it’s a wall in your house you’re thinking of decorating, the store at the Museum of Contemporary Art has a variety of art-based items, from $10 fridge magnets to mobiles based on Bauhaus and surrealist principles which would provide a dash of color to any room. Wearable Chicago souvenirs A sports mad city with professional basketball, ice hockey, baseball and American football teams, getting tickets to a game is an unmissable Chicago experience. And to remember it, what could be better than your very own jersey? Each stadium and arena have their own store, but you can also find items linked to all Chicago’s teams at stores including Clark Street Sports. So whether it’s an oversized foam finger or an official wristband emblazoned with the Chicago Cubs logo, odds are you’ll find it here. Thanks to an array of nationwide and boutique local stores, fashionistas can also take something home that will forever remind them of their time in the windy city. Independent Wolfbait & B-Girls is a marketplace offering the wares of 250 local artisans, including clothing you won’t find anywhere else and an almost endless pick of potential gifts. Other quirky establishments include Optimo Fine Hats, offering custom headgear for men whatever the occasion. Grabbing a T-shirt with the Chicago skyline will help your little ones remember their trip to Chicago, or make them want to visit themselves one day if they weren’t with you. Other items linked to the city’s architecture include ever-popular snow globes containing representations of the Willis Tower and Skydeck amongst other landmark buildings. Spend on the things that count with the best Chicago souvenirs The best Chicago souvenirs are those which continuously remind you of all the good times you had at the city’s attractions. That good time will be made all the better if you’ve visited them with Go City. Explore the city in this way and you’ll be able to take advantage of substantial savings on entrance admission to many of the top attractions and things to do. So why not check out our pass options and join the thousands of visitors who have already done just this?
Ian Packham

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