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Katie Sagal

A Week in Chicago for First Timers

Chicago is a fantastic city for a long vacation. 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. You can visit some, or all of these neighborhoods as part of a week-long vacation in Chicago. This list of suggested neighborhoods 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 Day, 2 Days/weekend getaway, and 3 Days in Chicago itinerary.

Magnificent Mile / River North

Big Bus Chicago Hop-on Hop-off Tour

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First-time visitors to the city, or those who haven’t been able to see and do a lot on previous visits, should definitely 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.


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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 history, the history of the city, and information about important events. This observation deck is located in the Hancock Tower, conveniently right in the middle of the Magnificent Mile attractions.

Mag Mile shopping

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 also a number of fun places just to window shop. Especially if you’re visiting in December, keep an eye out for creative holiday window decorations. Getting In: It’s free to stroll Michigan Avenue.

The Loop Attraction

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 to modern painting. Plus, they have some awesome gift shops, so souvenir shopping = solved.

Skydeck Chicago

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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.

They also boast 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 in 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's brand new exhibit space, coming in 2018.

Shedd Aquarium

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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 Chicago Cardholders get priority entry! This can save loads of time during the busy summer months.

Adler Planetarium

Get All-Access admission to the Adler Planetarium on your visit. 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

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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

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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 the 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

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

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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

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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

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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 if though you’ve gotten to know the fantastic Windy City. Choose from any of these top attractions to craft your perfect week in Chicago! Don’t forget – many of these top activities and attractions are available on the Chicago attractions passes, which can help you save up to 45% on combined admission versus paying at the attraction.

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