Skyline Chicago

A week in Chicago for first timers

How to spend a week in the Windy City
By Katie Sagal

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 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

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 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

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

cloud-gate-bean-black-white

Millennium Park

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

field-museum-chicago-brilliant-blue-sky

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

Shedd Aquarium

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

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

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

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

Classic Lake Tour

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

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lincoln park chicago
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Things to do in Lincoln Park Chicago

Dear reader! Do you like presidents? Do you like parks? Do you like doing fun things in a specific location? Well, you're in luck! Because Lincoln Park might just be the perfect place for you! There's so much to do in the area, you may never want to leave. So, whether you're a Chi-Town resident, or visiting from further afield, you might be wondering why you should visit Lincoln Park? We hear you, we see you, and we've got you covered. Read on, and discover our guide for all the things you can do in Lincoln Park, Chicago! Featuring: A trip to the zoo Tasty bites Get horticultural Go for a ride Feel historical and more! Lincoln Park Zoo Let's kick off this Lincoln Park funfest with a bit of animal action. Head to Lincoln Park Zoo if you want to hang out with sea lions, primates, and big cats too. They have a bunch of specific areas for you to explore, each with their own theme and group of animals to see. And, if that wasn't enough, there's also a host of rides and activities you can enjoy after you're all animal'd out. Join the Lionel Train Adventure to see more of the surrounding woodland, and join a cruise of the South Lake Lagoon and enjoy the ride! Perfect for big and little kids alike. Get some delicious food No matter what you're in the mood for, Lincoln Park's got your hunger under control. Grab some authentic Greek at AVLI Taverna, get classy with Alinea's tasting menu, or get some good old-fashioned deep dish pizza at Pequod's. In the market for some tasty beer to wash it all down? Head to Goose Island's Brew House. This world-renowned craft beer is Chicago born and bred, beginning back in 1988 at this very place. Lincoln Park Conservatory Want a little nature in your life? Take a walk to the Lincoln Park Conservatory. Not only will you find exotic species of flora from across the globe, but every plant and tree grown in the park starts here. Be sure to visit the four display houses, each showcasing different breeds of beautiful flowers and greenery. So, if you're visiting Chicago, it's definitely one of the best things to do in Lincoln Park! Bike ride Need to get the blood pumping? Why not ride your bike around Lincoln Park? If you don't have yours with you, rent one! It's a great way to get about and explore every nook and cranny of this massive green space. Better yet, bring some picnic supplies with you, find the perfect spot and set up your own snack bar. Nothing quite beats lounging on the grass and enjoying a delicious snack! Second City Hilarity Need a bit of a pick-me-up? Well, they say laughter is the best medicine. Put that theory to the test at Second City. The home of sketch and improv comedy, every night, you'll discover a hilarious act or two performing on stage. But don't take our word for it. Comedy greats like Bill Murray, Tina Fey, and Steve Carrell cut their teeth on Second City's stage. Why not discover comedy's next big thing today? Chicago History Museum Want to learn a little more about Chicago's history? You'll want to stop by the Chicago History Museum! Learn how the city grew from a humble town to the metropolis it is today. Discover the events that shaped it, like the Great Fire of 1871. And find out more about our favorite president, and the namesake of the very park, Abraham Lincoln. Nourish that withered pea you call a brain with some succulent knowledge and information. Hit the beach If the weather is fine and the clouds are away, why not go to the beach, even just for a day? Just a stone's throw from Lincoln Park is North Avenue Beach, one of the city's most popular spots come summertime. Find a stretch of sand, lay down a towel, and get your tan on. Or, go take a dip in the ocean. Just remember to pack some sunblock. Chicago already has enough lobster. Go see Lincoln And why you're there, why not go and see the man himself? Head to the Lincoln Monument and go tip your hat to one of the greats. There, you'll find the Standing Lincoln sculpture, a beautiful crafting of Abraham Lincoln, standing before his presidential chair. Standing at a whopping 12ft tall, and designed by Irish sculptor Saint-Gaudens, it's a must-visit in Lincoln Park. Connected to the statue are delightful gardens, so feel free to walk around and take it all in. Stroll through Oz Park No, you're not in Kansas anymore. Or, maybe you never were. Anyway, if you're a fan of the weird and wonderful Wizard of Oz, you owe it to yourself to take a stroll through Oz Park. As you may have guessed, it's themed around the book and film of the same name. You'll see statues of all the main cast, including Dorothy, Tin Man, Scarecrow, and the Cowardly Lion. There's plenty for kids to do too, including day camps, tennis and basketball courts, and a big garden called Dorothy's Playground. Green City Market And finally, let's end this list of things to do in Lincoln Park, Chicago with some food. Glorious food. Do you like your food fresh and your produce local? Then go check out Green City Market! It's a market dedicated to sustainable farming, and ensures all food is sourced from environmentally-conscious farmers. Visitors will be welcomed by a host of stalls selling everything from fruit and vegetables, to premade meals you can tuck into in the park. There's also a big focus on education, so you can learn about sustainable farming and where to buy groceries. And that's our list of the best things to do in Lincoln Park, Chicago! Are you visiting Chicago from out of state, or across the pond? You might want to read our guide to getting around the city. Coming by yourself? We've got you covered. And if you're thinking about heading to Chinatown, you absolutely should! Here's everything you need to know for your visit.
Dom Bewley
chicago in may
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Chicago in May

Spring has sprung, and summer is just around the corner. That big yellow ball in the sky isn't so shy anymore. That's right y'all, it's May. Time to shuffle off the light jackets and risk it in just a t-shirt or summer dress. Whether you're hitting the Windy City for a vacation, or a resident wondering how to spend the newfound warmth, never fear! This list caters to you all. Scroll down, and find out what you shouldn't miss in Chicago in May. Featuring: Skydeck Chicago River Cruises Navy Pier funfair Bike rides The Zoo and more! Chicago in May: What to Expect May is when temperatures will start to climb. Generally, you'll find tops of around 68-70°F, or 20-21°C, and dips of around 50-51°F, or 9-10°C. So, pack some lighter clothes for the days, and some warmer jackets and sweaters for the nights. There's a chance of rain too, so pack your best umbrella, just to be safe. Chicago in May: What to Do Skydeck Chicago Looking for thrills, buddy? How about heading up to the 103rd floor and overlooking the city at over 1,300ft? If that sounds like just the ticket, then check out Skydeck Chicago! Formerly the Sears Tower, Skydeck gives you amazing views across the city and beyond. In fact, you can see four different states from the viewing platform! Spot key Chicago landmarks, and if you dare, head out onto The Ledge, a see-through, glass-floored platform. See the city right beneath your feet. Not for the faint of heart, but if you've already made the journey up to the top, why not go the extra step? We dare you. Then, when you're done, ride the Multimedia elevator all the way down to terra firma, and learn about landmarks as you pass them. Shoreline Architecture River Cruise Do you like water? Not just inside your body, but outside too? Does the thought of riding Poseidon's waves while seeing some sweet buildings get you giddy? Well, check this out. Hop aboard a Shoreline Architecture River Cruise and do just that. Chicago in May is the perfect time to catch a ride. The city has heaps of interesting architecture to see, including works from building men like Goldberg and van der Rohe. Plus, you'll learn about the Great Fire in the 19th century that helped shape the metropolis it has become today. Make sure you take some sweet snaps for your social media, so people think you're cooler than you really are. Learning and boats - does it get much better than that? Navy Pier Do you like rides? Are you looking for an exhilarating experience in the city? Then you're looking for none other than Navy Pier. This 50-acre seaside locale is one of the biggest tourism draws in Chicago. Perhaps the pier's biggest attraction is the Centennial Wheel, a colossal Ferris Wheel that towers over the boardwalk. Rising to over 200ft at its peak, you'll get amazing views all the way to Lake Michigan. And, if those pesky clouds show their grey faces, never fear, as each gondola is a closed unit. On top of all that, there are plenty of other rides to try out, bites to eat, and drinks to wash it all down. Pick up a souvenir while you're at it. Stop by the Zoo Why not make the most of the May weather by visiting the zoo in Chicago? Lincoln Park Zoo is a wonderland of animals, with thousands to see and meet. There's the Sea Lion Pool where, shock horror, the sea lions hang out. Or, if you like your mammals landlocked, there's the Center for African Apes, with an assortment of apes and gorillas to see. Then, head into the lion's den at Kovier Lion House, which houses more big cats than you could shake a paw at. Beyond that, you can take a cruise of the South Lake Lagoon, or check out some of the rides. The Lionel Train Adventure is perfect for kids, taking passengers on a trip to explore the surrounding woodland. There's also the Endangered Species Carousel, where riders can hop aboard nearly 50 replicas of endangered animals and help raise awareness of their plight. Then, grab a bite at the cafe, or pick up a stuffed animal for the little one. Bike and Roll Want to see the sights in Chicago, but make the most of the May weather? Then hop on a two-wheeler and get some exercise while you're at it! Hire a bike, and go exploring. Glide beside Chicago's lakefront, discover the city's many trails and green lanes to avoid traffic, and see all the city's wonders while breathing in that great fresh air. Bring some food and a few drinks, find a spot to settle, and put together a mid-ride picnic. A great way to spend a sunny day in the windy city. Play ball If you're a sports fan, you may have heard of the game they call 'baseball.' One person throws a ball, the other hits it with a bat, and then everyone runs around trying to catch it. That about sums it up. Well, if that sounds like you, then you'll be well aware of the Chicago Cubs. A trip to their stadium at Wrigley Field might appeal to all sports fans, as the atmosphere is notoriously infectious. And not in the mask-wearing, 6ft apart way. This century-old ground is home to baseball games throughout the year, so why not check one out and see what all the fuss is about? Get flowery Fancy yourself a bit of a Greenfingers? Then you might be interested in a visit to one of the country's biggest and best botanical gardens! The Garfield Park Conservatory houses thousands of flora beneath its glass dome, and in May, it's the location of the 2022 Spring Flower Show. So if you want to see some award-winning tulips, daffodils, and other flowers you know and love, go check it out! Relax and see the city If you want to give those dear legs of yours a rest, why not hop on a bus and get a tour of the town? A Gray Line Chicago Grand Tour takes you around all of the city's biggest landmarks, including Orchestra Hall, Lake Point Towers, and Lincoln Park Conservatory, all the way to Grant Park. You even have the opportunity to hop off and go exploring at certain points, as long as the bus isn't delayed! And that's everything you need to know about Chicago in May!
Dom Bewley

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