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! 

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Katie Sagal
Go City Travel Expert

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Chicago Art Museum Tickets & Tips for Visiting

Planning your trip to Chicago? During your visit there is one place on Michigan Ave that is a definite must see destination. The Art Institute of Chicago was recently voted as the #1 Museum in the World by TripAdvisor. The museum houses a spectacular array of over 300,000 works, from modern and contemporary, architecture, design, and photography to ancient artifacts, and Impressionist paintings by Monet. Check out our helpful guide for visiting Chicago's art museum, (the Art Institute of Chicago) packed full of ways to save on admission, tips for visiting, other nearby attractions, and much more. Looking for Chicago Art Museum Discount Tickets? We’ve got you covered – Art Institute of Chicago admission is available with the below money saving options, so you can choose the attraction pass that’s right for you: 1. All-Inclusive Pass – All you can do. Includes admission to dozens of attractions. 2. Explorer Pass – Choose as you go. Includes admission of up to 5 attractions. 3. Build Your Own Pass – Select the attractions you want to visit prior to visiting. See all available passes, attractions & prices – Learn more. Recently Voted #1 Museum in the World by TripAdvisor! Best Times to Visit If you can, plan to visit the Art Institute early on a weekday, between noon and 3 pm, when there will likely be fewer people there. Before you go inside make sure to check out “In an Attitude of Defiance” the lion on the south side, and “On the Prowl” his north side sibling. Nearby Attractions Places to Eat Nearby Ge Pa De Caffe is located across the street from the museum and Millennium Park. You can't forget to order a latte while you're there. Seven Lions Is also located across from the museum. They offer American cuisine at its best. Known for their excellent brunch fare, they are moderately priced. Need to Know Hours Friday-Wednesday, 10:30 am-5:00 pm. Last admission at 4:30 pm. Thursday, 10:30 am-8:00 pm. Closings: Thanksgiving Day, Christmas Day and New Year's Day. All holidays and hours are subject to change without notice. Getting In If you purchase a Go Chicago Card, enter from Michigan Avenue using the middle set of doors labeled Fast Pass. You may also use the Modern Wing entrance on Monroe Avenue. Look for the Fast Pass signs once inside to skip the line. Directions & Address 111 South Michigan Avenue (at Adams Street) Chicago, IL 60603 Public Transportation: Take CTA: Brown, Orange, Purple, Pink, and Green lines to Adams St./Wabash Ave. stop. Red and blue lines to Monroe Street. Metra to Van Buren/Jackson and Buses #3, 4, 6, 7, 14, 126, 145, 147, and 151 to the museum. Save on Tickets with a Go Chicago Card Remember, the Go Chicago® Card is the best choice for maximum savings and flexibility, which includes Art Institute of Chicago tickets, plus admission to your choice of other top attractions. Save up to 55% on top museums, tours, and activities vs. paying at the gate. Visit multiple Chicago attractions for one low price.
Lindsay Eagan
Rainbow crosswalk in Boystown, Chicago
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Things to do in Chicago for Pride Day

The Chicago Pride Parade is one of the most highly attended festivals of its kind on the planet, pulling in something like a million revelers every year. No surprise really, given Chicago is one of the most LGBTQ-friendly cities in the States, its Northalsted neighborhood (aka Boystown) a vibrant community hub that was the first in the country to be officially recognized as a gay village. The city’s colorful month-long June Pride party is, as you might expect, a fairly flamboyant affair, taking in karaoke nights, drag brunches, art shows, skate parties, marching bands, club nights and much more. Raise your rainbow flag and read on for our guide to some of the best things to do in Chicago during Pride month. Spend the Day in Boystown There’s no better way to familiarize yourself with Chicago’s LGBTQ+ history and culture than with a visit to the Legacy Walk in Boystown. Take a stroll along the North Halsted Street Corridor between Belmont Avenue and Grace Street, where this unique open-air museum takes the form of 35-or-so steel ‘rainbow pylons’. Each standing 25 feet tall, the pylons act as monuments to those legends who helped shape the LGBTQ+ movement in Chicago and beyond, with bronze plaques commemorating individuals including James Baldwin, Josephine Baker, Harvey Milk, Oscar Wilde, Jose Sarria and Freddie Mercury, plus pivotal events like the 1969 Stonewall Riots. Afterwards, make time to check out some of the neighborhood’s other beloved LGBTQ+ hotspots, including the Center on Halsted, a community hub that’s home to the Hoover-Leppen Theater and Billie Jean King Recreation Hall among other facilities. Head up to the roof for tip-top neighborhood views that become yet more colorful during Pride month, thanks to the increased proliferation of rainbow flags and bunting that decorate the streets below. Hungry? You’re in luck. Boystown also happens to be home to some of the best brunch spots in town. Hit up local institution Drew’s on Halsted for eggs every which way accompanied by breakfast martinis and live DJs. Or mosey on over to the smart, literary Wilde Bar & Restaurant, named after guess who? Of course, the LGBTQ+ nightlife in this lively enclave is just about as good as it gets, running the gamut from karaoke parties to dive bars, drag nights and hedonistic all-night dance parties. Try Sidetrack, The Closet, Roscoe's, Hydrate and the Kit Kat Lounge for some of the very best. LGBTQ+ Art & Culture There’s plenty more going across Chicago through the month of June. Check press listings for comedy, cabaret and drag performances hosted by the likes of Boystown stalwarts the Newport Theater, Dorothy and the Whiskey Girl Tavern.  Many of the city’s largest cultural institutions also run LGBTQ-themed programs and exhibitions during Pride month. For example, the Field Museum, one of the biggest and best natural history museums in the world, hosts an annual drag pageant as well as events around the role of sex and gender in the natural world.  Meanwhile, the American Writers Museum runs readings, workshops and tours spotlighting the work of LGBTQ+ authors whose writings are exhibited here, including the likes of James Baldwin, Maurice Sendak and Susan Sontag. There are events for kids at Chicago Public Library branches including Logan Square and South Shore, with drag and rainbow story times to keep the little ‘uns entertained, and an annual party down at Navy Pier, which is usually held the day before the Pride march. It’s an all-day event that features live music, marching bands, DJs and more, and is conveniently close to all those seaside fairground rides for a spot of old-school fun and relaxation between bouts of dancing! General admission to a number of these attractions (plus many more tours and activities around Chicago) are included with a Go Chicago pass. You could save up to 50% on entry to the likes of Navy Pier, the Field Museum, the Shedd Aquarium, 360 Chicago and more. Note that additional tickets may be required for entry to some Pride-themed events. Find out more about the Go Chicago pass and get yours here. The Pride Parade and Festival As the climax of Chicago’s Pride month approaches, all attention turns towards Chicago Pride Fest and the annual parade. The Parade takes place on the last Sunday of June with Pride Fest traditionally falling on the Friday and Saturday of the same weekend (or sometimes the weekend before). Pride Fest gets the party started in earnest with two days of live performances across three stages, everything from international pop stars to the very best of Chicago’s DJ and drag scenes. Add to that 150+ food and beverage vendors and you have all the ingredients you require for a top shindig. The festival takes place on Halsted Street, from Addison to Grace St, and is free to enter, though there’s a suggested $15 donation to help pay performers and festival workers, as well as supporting local community programs. Big-name stars to grace the stages here include M People’s Heather Small, Natasha Bedingfeld, Chaka Khan, and the Chicago Gay Men’s Chorus. Find out more about this year’s Pride Fest, including the entertainment line-up, here. The main event takes place on the last Sunday of the month, and draws the biggest crowds of the month. The Chicago Pride Parade sets off from around Sheridan and Broadway at 11AM, painting a rainbow across Northalsted as it weaves its way along and around Halsted to Lincoln Park – a distance of over six kilometers. Nab your spot to watch as dozens of flamboyant floats, revelers in outlandish costumes and live performers cruise past, complete with marching bands, stilt walkers, drag kings and queens, and more. The area surrounding Belmont and Addison stations tends to get the most busy, so arrive early if you want a decent view, or bodyswerve it altogether if claustrophobic crowds ain’t your thang. Rest assured there are plenty less densely packed locations: you’ll find for example that you have a little more breathing space towards the start of the route, and on its east side. Find about more about this year’s Chicago Pride Parade here. Save on Chicago’s Most Popular Attractions Don’t miss the opportunity to check out some of Chicago’s top tours, activities and attractions while you’re in town. You could save up to 50% with a Go Chicago pass. Find out more and choose yours here.
Stuart Bak
Stuart Bak

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