Thinking about visiting the Windy City for the first time? You’re in for a treat! As a local, I can tell you that Chicago is one of those places that’ll grab you by the heart and refuse to let go. You’ll want to come back again and again.
But Chicago can also be a bit overwhelming for first-timers. There’s just so much to see and do. That’s why I’ve put together this ultimate guide to help you navigate the city like a pro. We cover everything from must-see landmarks and family-friendly attractions to the best tours, hidden gems, and of course, where to find the best Chicago food.
So grab a cup of coffee (or a slice of deep-dish), and let’s explore the best of the city in this ultimate Chicago guide to food, fun, and memory-making.
Chicago’s top landmarks for first-timers
Illinois’ cultural capital offers a unique take on the city life of America. With more theaters than NYC and a rich history, you’ll find plenty to last a lifetime, let alone a weekend visit.
But if you’re short on time or just want to cut to the good stuff, As you go, be sure to keep an eye out for these 12 must-see landmarks.
- Following the Chicago River, the popular Chicago Riverwalk meanders through the city center with intriguing views, delightful stopovers, and beautiful public art.
- Nestled in the northern end of downtown Chicago, the Lincoln Park Zoo offers a free visit to one of the best zoos in America. Grab a snack from vendors, bring your own picnic, or just enjoy the beauty of the zoo and surrounding park.
- Enjoy the Beluga whales, dolphin show, otters, and much more at the incredible Shedd Aquarium of Chicago. The incredible aquarium offers some of the most stunning habitat displays, best learning opportunities, and hands-on experiences you’ll find anywhere.
- Walk, bike, or grab a Lyft down to the Navy Pier for beautiful views of the Lake, boat rides, museums, IMAX theater, shopping, cultural events, and much more any day of the year.
- Whether you’re into biking, running, or walking, the Lakefront Trail of Chicago will get you there. Winding its way along the shore of Lake Michigan from Edgewater neighborhood down to Hyde Park, the trail welcomes locals and visitors alike with exciting activities, stunning views, and easy access to anywhere on the east side of Chicago.
- One of the most iconic and popular destinations in all Chicago, the Museum of Science and Industry is the place to be any time of year. Enjoy the permanent and changing exhibits depicting the intriguing aspects of today’s world and the history of technology, science, and industry.
- The iconic Chicago Theater welcomes guests and performances from around the world in the State Street venue.
- One of the most iconic buildings in Chicago, the John Hancock Center now hosts 360 Chicago, a premier attraction of the city. For great views, head up to the top.
- Another iconic site, the Willis Tower Skydeck (formerly, the Sears Tower) offers incredible views of the city from plexiglass boxes over the streets below. Go up for magical sights night or day.
- Check out the Cloud Gate (or “the Bean”), the Crown Fountain, ice skating, floral displays, rock climbing, and public art at Millennium Park on Michigan Avenue. The park welcomes some 5 million visitors each year.
- Near Millennium Park you’ll find the world famous Art Institute of Chicago where dazzling works of art from around the world go on display. See classics like Van Gogh or modern works from emerging artists, all in one place.
- On the west side of the city, Garfield Park Conservatory is one of the most impressive and beautiful spots in the city.
And here’s a bonus. Once the hotspot for Al Capone and friends, The Green Mill in Uptown remains a highlight for jazz and other local musicians, along with great eats, and fantastic entertainment just about every night of the week.
What to see in Chicago with families
Whatever the age of your family, Chicago has some of the best family-friendly attractions in the nation. Museums, parks, and kid-focused attractions all offer great spots for you to build memories together.
Top Chicago museums
Apart from the most visited museums like the Art Institute of Chicago and the Museum of Science and Industry and the Field Museum, the city has numerous other intriguing museums and cultural centers to explore.
Writers and readers — anyone fascinated with literature and the written word, really — will enjoy visiting the unique American Writers Museum on Michigan Avenue. Explore the unique exhibits centered around the written word, enjoy story time, or, if you’re lucky, make it in for the Writer’s Festival in the springtime.
Hosting numerous events year round, housed with some of the most stunning architecture of the city, the Chicago Cultural Center is one of the most amazing sights to see in the Windy City. Explore the glorious stained-glass domes while participating in the cultural events held regularly throughout the year.
One of the most famous and beloved museums in Chicago, for all ages, is the Field Museum. Explore the unique natural history of Chicago area’s through 20 permanent exhibitions and new, exciting traveling exhibitions any time of the year. Find the famous Sue the T. rex, along with the new museum’s titanosaur skeleton greeter “Maximo” in the lobby.
Look to the stars at the Adler Planetarium, a favorite museum on the Museum Campus on Lake Michigan. You’ll find unique programming, beautiful scenic views of the night sky in the Grainger Sky Theater, and brilliant space-themed exhibitions throughout the space.
Curious about the life of the Second City? Visit the Chicago History Museum to learn about all things Chicago and times long past.
Best Chicago parks for travelers
One of the things locals love most about Chicago is the plethora of parks the city holds. From massive parks to tiny sidewalk oases, the Windy City offers spots for respite in every neighborhood.
I already mentioned Millennium Park — and it’s a classic — but here are some others to add to your Chicago visit.
- Located near Millennium Park, Maggie Daley Park, and the lakefront, Grant Park offers not only fabulous public art, walking trails, and views of the city, but contains the world-famous Buckingham Fountain.
- On the north end of the city, along the shore of Lake Michigan, Lincoln Park encompasses the largest park campus in the city. Numerous attractions reside within the park, including parts of the Lakefront Trail, the Lincoln Park Zoo, Lincoln Park Conservatory, Peggy Notebaert Nature Museum, and the Alfred Caldwell Lily Pool.
- Enjoy trails, native plants and wildlife, special events, stunning views of the city and lake, picnicking, public art and more on the unique park of Northerly Island.
Popular Chicago markets and squares
The Navy Pier functions as a family-friendly market square, but the city has many other offerings where options abound.
The famous Daley Plaza offers public art (including a giant sculpture made by Picasso that no one knows what it means) as well as event space and gathering spots for just about any season. You’ll often also find food trucks parked near the square, where you can grab some tasty treats for the whole family.
Another favorite, Logan Square offers boutique shopping, restaurants, and a delightful farmer’s market in the warmer months each year. Enjoy walking the residential neighborhood nearby where parks abound.
Best Chicago tours to get to know the city
Amazing Chicago tours take you through the history, artwork, and incredible architecture that have helped shape the unique culture of the Windy City. Our local-led Chicago tours do just this, with delightful views along the way.
The best tours in Chicago include:
- An architecture walking tour along the Riverwalk, where you’ll not only see the gorgeous or intriguing buildings that help Chicago’s distinctive aesthetic, but views of the river, Lake Michigan, and the curated garden-like state of the esplanade along the river.
- The haunted history and Chicago mob past have helped to create a unique culture in the Second City. Take the Haunted Mysteries of Chicago Mob Tour to get the full flavor.
Best shopping in Chicago
If you enjoy shopping, you’re in luck. Nearly every neighborhood in Chicago has its own shopping district. Many flourish with boutiques or malls nestled in among the fantastic restaurants.
Some of the best spots for shopping include:
- Wicker Park where boutiques and locally owned shops abound
- The Gold Coast with the Magnificent Mile and Water Tower Place for high-end shopping
- Old Town buzzes with unique experiences, boutiques, and eateries
- State Street and the Loop provides all the high-end shopping you could want
When is the best time to visit Chicago?
I live here year-round, and I can tell you there’s really no bad time to visit Chicago. Certain times of year, of course, will lend themselves more to specific kinds of attractions, outings, and fun.
In recent years, the coldest weather has been found in late February to early March, usually starting to warm up around St. Patrick’s Day, though it could still be a bit chilly, so check the weather forecast closely before packing.
The summers are warm to hot during the day, nights usually cooling off in June, early July, and mid-September. Autumn is lovely, but snow may come as early as late October. Spring and autumn are vibrant with flowers and fall foliage, but Christmas in Chicago is one of the best times to enjoy the city as a whole. The town really puts on the display each year to celebrate.
Where to stay when you visit Chicago
There are primarily two ways to plan your location for Chicago visits.
If you’re on a tighter budget, stay in the neighborhoods at one of the hotels, youth hostels, or budget-friendly motels. These spots connect you to downtown and all the attractions easily via public transit.
If you’re looking for that downtown experience, grab a stay in Gold Coast, River North, the Loop, or Streeterville. These higher-end locales will keep you close to the main attractions.
Chicago’s best events
Chicago is known as a city of festivals. The whole region, in fact, hosts festivals of all kinds from January to December each year, celebrating the diversity of the residents, the flavors of the local cuisine, and gifts and talents of performers, writers, and artists of the area.
Here’s a roundup of Chicago events by season, but it’s not comprehensive. There’s a lot going on here. But these highlights should get you started.
Winter
- Christmastime in Chicago is marked by the famous Christkindlmarket in Daley Plaza and bonus locations added each year. Find European-style decor and gifts for the holidays, crafted by highly-skilled artisans.
- Ice Skating at Maggie Daley Park, Millennium Park, and other public locations throughout the city are the highlight for many locals and visitors alike. The season usually opens in November and ends in January or February, depending on the location.
- The Winter Flower Show at Garfield Park Conservatory offers some of the most uplifting and gorgeous sights of the chill winter season. Breathe in the fragrance of flowers and take a stroll through one of the prettiest spots in the city.
Spring
Lush with vivid flowers everywhere, spring in Chicago is one of the most beautiful times to enjoy the outdoor spaces of the city. Start with some of the markets at festivals.
- The Chicago Latino Film Festival offers the opportunity to watch and learn more about the culture of Latinx in Chicago and around the world through unique viewing experiences and informative presentations.
- Enjoy a European-style outdoor market known as the Randolph Street Market. Find incredible antiques, vintage goodies, decor, fashion, artisan wares, and much more.
- Venture to the Lakeview neighborhood for the Belmont Sheffield Music Fest, which is basically a huge block party with beer and wine vendors, artisans, and tribute bands.
Summer
Summertime in Chicago is peak season for all the festivals. Enjoy dance, food, Pride celebrations, and music all summer long.
- What could be more Chicago than the Windy City Hot Dog Fest? Try offerings from the many hot dog vendors of the city, enjoying their unique take on the Chicago Dog.
- Chicago’s particularly known for its blues, so why not pop in for the Chicago Blues Festival, one of the best in the world.
- Perhaps the most famous festival of Chicago is Lollapalooza, the music fest in August that attracts thousands every year, thanks to the numerous well-known artists and local bands that perform each season.
- Chicago has an amazing Pride celebrating each year, with Pride in the Park as one of the most exciting experiences of all. Come celebrate with flair each June.
- For those who love a good dance, head to Grant Park for Chicago Summerdance. Take a free group lesson, find a partner (or bring your own), and enjoy the many styles of music and dance throughout the summer.
Fall
Crisp, cool breezes flutter the leaves of Chicago trees, announcing the time for some of the most beloved festivals and events in the city.
- Jazz lovers rejoice in the Chicago Jazz Festival that happens each year in Millennium Park. The festival centers on incredible jazz, with food, educational programs, and more bringing it all to life.
- Foodies love the Taste of Chicago, the biggest food festival in the city. You’ll find vendors from all over, in all flavor profiles, providing tasting options for their food and beverages.
- Book lovers flock annually to the Printers Row Lit Fest where authors, aspiring writers, publishers, literary agents, and magazine reps show up with the latest releases, author talks, and industry know-how.
Best food in Chicago
The best Chicago dog is highly controversial, and I’m not about to start a food fight. I’d say you can’t go wrong with a hot dog from Fred & Jack’s. They’ve been serving dogs since the 1940s, so they’re clearly doing something right, and it’s a budget-friendly meal for the whole family. Of course, if you want the OG, the oldest hot dog stand in town is Dave’s Red Hots, opened in the 1930s and famously not allowing ketchup because they say it ruins the taste. (This is a theme throughout Chicago actually — we think you should put mustard on your dog.)
Speaking of beef, you’ve got to order an Italian beef sandwich, affectionately known as a “Soggy Sandwich,” while here. They’re packed with thinly sliced roast beef and drenched in savory au jus. Sticking with the classics, I recommend Al’s Beef, opened in 1938.
Like Chicago dogs, the best Chicago deep-dish pizza is hotly contested. There isn’t just one place to get this quintessential Chicago dish. There are dozens. For vintage vibes with plenty of locations to choose from, try Giordano’s. They have a smooth sauce and a serious tall pie that is packed with more cheese than you should eat in a month. Enjoy!
How long should I spend in Chicago?
Good question! To hit all the highlights, plan on 3-5 days in Chicago.
If you want to explore the neighborhoods and really enjoy the city, take your time and plan for a full week to take in all the sites, food, theater, concerts, and maybe even take a day trip to Starved Rock State Park or hit up the Ravinia Music Festival in the summers.
Chicago transportation for travelers
The best way to get around Chicago is walking, mixed with public transit for greater distances. Take the Red or Brown Line to the Loop, hop off, and start strolling! You’ll find amazing eats, beautiful scenery, fantastic parts, fabulous shops, and intriguing attractions at every turn.
Many buses run 24-7, though smaller routes run less often — always check the schedule before counting on a given bus.
The Elevated Train or ‘El’ has various schedules, based on the color schedule.
- Red Line – all day every day, including weekends and holidays
- Blue Line – all day every day, including weekends and holidays
- Brown Line – Weekdays 4 a.m.-1:30 a.m.; weekends/holidays 5 a.m.-1 a.m.
- Pink Line – Weekdays 4 a.m.-1 a.m.; weekends/holidays 5 a.m.-1 a.m.
- Orange Line – Varies by day (check schedule)
- Green Line – Varies by day and the route splits (check schedule)
- Purple Line – Varies by day (check schedule)
- Yellow Line – Weekdays 5 a.m.-11 p.m.; weekends/holidays 6 or 6:20 a.m. to 11 or 11:15 p.m.
Exploring the best of Chicago
As I said when I started, that’s not all, folks. There really is so much to do in America’s third largest city. My advice? See it with a local. Our Chicago tours show you the best of the city with the little-known stories — architectural highlights or mob secrets — that you might otherwise miss.
Before I go, let me give you the inside scoop on some hidden gems you might enjoy. If you’re a film buff, don’t miss the Music Box Theatre, vintage cinema that shows indie and classic flicks. For bookworms, Myopic Books in Wicker Park is a three-story paradise of used books where you can get lost for hours. Into quirky art? Intuit: The Center for Intuitive and Outsider Art is your spot, or you might enjoy the L H Selman Glass Gallery. Prefer history? Stop by the Institute for the Study of Ancient Cultures at the University of Chicago.
And if you want to experience some authentic Chicago nightlife, hit up Phyllis’ Musical Inn in Wicker Park — it’s been around forever and has great live music.
Lastly, be sure to take a stroll through Andersonville. It’s a Chicago neighborhood with a cozy, small-town feel alongside amazing Swedish bakeries and unique shops.
Chicago is all about exploring and stumbling upon unexpected delights. So don’t be afraid to wander off the tourist trail. Now get out there and experience my city like a true Chicagoan!