Welcome to Experience Gifts' guide to Chicago, updated for 2022!
After New York and Los Angeles, Chicago, the capital of the state of Illinois, is the third largest city in the United States, home to almost three million people.
Known for its deep dish pizza, 1920's gangster past, and 25 miles of golden beaches, Chicago is a city that has something for every personality, whether you’re planning a family weekend away or an epic birthday bash. Split into 77 communities over 234 square miles, there’s lots to see and do across the entire city, with each neighborhood bringing its own cultural heritage and unique vibe to the mix.
Trying to see all of Chicago in one trip is ambitious, so we’ve narrowed the list to our favorite experiences in our top ten favorite neighborhoods, from the ultimate must-do tourist attractions to the hidden gems that are popular with locals. Read on for top pick restaurants, sightseeing tours, comedy clubs and more! We've updated our guide with some new additions for 2022, so there's even more to discover.
| Logan Square
Located around 6km inland from the Lake Michigan shoreline, Logan Square is a trendy neighborhood with popular music venues, art galleries, breweries and hipster coffee shops lining the streets. Since 2005, the Logan Square Farmers Market has been welcoming tourists and locals alike to browse the 80+ vendors, operating every Sunday throughout the year.
From homemade honey to organic fruit and vegetables, from sustainable meat to freshly baked pastries, the open-air market is a joy to discover and can easily take the full 10am-3pm to explore. Don’t miss a chance to see USA Today’s ‘Best Farmers Market in Illinois’ on your next trip to Chicago!
| West Loop
If you’re visiting Chicago for the first time, you’ll probably hear a lot about the Chicago Loop, the elevated rail circuit that serves as the city’s main transport connection. The Loop forms Chicago’s downtown, which in itself is split into North, West, and South sides, which are also made up of communities and neighborhoods that bring their own downtown flavor – did we mention Chicago is really big?
West Loop, not having the shoreline to push real estate prices up, is packed with hip markets, laidback diners, and plenty of bars. Discover this neighborhood on a West Loop Pub Tour, exploring the history of the area and it’s Greek heritage between stops at popular pubs and bars – the best way to sightsee!
| Little Italy
Nestled alongside the West Loop region is Chicago’s Little Italy, a quaint neighborhood with plenty of green spaces, entertainment venues, and of course a fantastic variety of family-owned Italian restaurants.
Along the central W Taylor St you’ll find the cafeteria-style Pompeii, the best Italian donuts at Scafuri Bakery, authentic Italian ice-cream at Mario's Italian Lemonade, and our personal favorite; The Rosebud. Established in 1976, the dark wood and white-tablecloth restaurant serves up classic Italian dishes like eggplant Rotolo, fresh ravioli, pappardelle bolognese, and lots more in generous portions with family-friendly service.
We love the look of this Little Italy tour, run by Chef Driven Food Tours. Join a local guide for a flavorful tour through the neighborhood's most outstanding restaurants, and learn the fascinating history of the Italian immigrants who made the area what it is today.
We recommend loose pants for this one!
| South Loop
Chicago’s South Loop neighborhood is one of the busiest, oldest, and most densely populated regions of the city, boasting the three biggest museums in Chicago and America’s first planetarium; The Adler Planetarium.
Amongst the classic red-brick structures that line the South Loop streets is Glessner House, an architecturally significant 19th century home that’s now open to the public as a museum, providing regular tours, discussions and exhibitions to tourists and Chicagoans alike.
The House is dedicated to the preservation of historical design and culture, and is a great choice for anyone fascinated by the development of architecture throughout the centuries.
| Near North Side
Popular tourist attractions often receive a lot of criticism for having long lines and high ticket prices, but they must be popular for a reason, right?
New York City has the Empire State Building, San Francisco has the Golden Gate Bridge, Los Angeles has the Hollywood sign; and Chicago has the 875 North Michigan Avenue Building. At 100 storeys high, the super tall skyscraper looms over Chicago’s main commercial district, the Magnificent Mile, and features an observation deck on the 94th floor, skyline tours, yoga classes, happy hour overlooking the city, and the famous Tilt experience.
The first of its kind, Tilt invites guests to see Chicago like never before, extended over glass 1,030 feet above ground. A great family experience, and kids go free on Sundays!
| Lincoln Park
Speaking of fun family activities in Chicago, we’re heading north to the Lincoln Park neighborhood, home to the Lincoln Park Zoo. Chicago’s largest city park, Lincoln also houses the Peggy Notebaert Nature Museum, the Lincoln Park Conservatory, and the picturesque Fullerton Beach, making it the perfect choice for a quick escape from the city.
Lincoln Park Zoo is free to enter and houses everything from African Penguins to Zebra Tilapia, plus child-friendly activities like farmyard play days, sing-alongs, and a Breakfast With The Animals experience – ideal for budget-friendly Chicago days out!
| Old Town
At the southern end of Lincoln Park is Chicago’s Old Town, a historic neighborhood centred around St. Michael's Catholic Church, one of the few buildings to survive the momentous Great Chicago Fire in 1871 which destroyed over 17,500 structures.
On Old Town’s main high street is the iconic The Second City, Chicago’s premier comedy club that hosts improv shows, interactive sketches, and performances from famous faces. With alumni including Steve Carell, Joan Rivers, Bill Murray and plenty more, you can be sure of top quality acts and big belly laughs at this Chicago institution. Check out their events calendar and make sure you pay a visit!
| Chinatown
Chinatowns across the country are popular with tourists who enjoy the culture, community, and food of the region, and Chicago is no exception.
Chinese migrants fled California in the 19th century and settled in Chicago, making it the second oldest Chinatown in the US and one of the largest with over 70,000 residents. Discover Chicago’s Chinatown in all its glory on a three hour food tour hosted by Chicago Food Planet, joining a knowledgeable and entertaining guide for a gastronomic excursion round five specially-chosen establishments.
Visit notable landmarks, learn Chinese customs, and taste some of the best sweet and savory dishes imaginable – the ultimate Chicago Chinatown experience!
| Marshall Square
Known for its Mexican community and vibrant Latin-American culture, Marshall Square is a small neighborhood with a great food scene and energetic nightlife. At the southern end of the family-friendly Douglas Park is the Lagunitas Brewing Company, one of the top selling breweries in the United States. With regular live music performances, brewery tours and tastings, and a modern taproom and restaurant, Lagunitas is a Marshall Square gem that attracts visitors from miles around.
Beer-lovers planning a trip to Chicago won’t want to miss a visit to Lagunitas, so book a tour, catch a show, or simply sit back and enjoy one of the ever-changing limited addition brews on offer!
| Streeterville
Many Chicago neighborhoods are defined by the Chicago River and its various canals, so we wouldn’t be doing a neighborhood article justice without paying tribute to the remarkable force of nature that created the city as we know it. Streeterville sits on the northern side of where the Chicago River meets Lake Michigan, and is where you’ll find famous landmarks including The Wrigley Building, the Tribune Tower, and many other structures that make up the Chicago skyline.
Admire Chicago architecture from a new perspective on a 90 minute Chicago River Boat Tour, cruising along the canals whilst enjoying historical commentary, points of interest, and fun facts on all things Chicago. A fun experience to book at the start of a Chicago trip that’ll start you on the right track!
New for 2022: Fit in some exercise while you see the sights of Chicago, during this Chicago River Yoga Walking Tour led by a friendly yogi guide. You'll meet your guide near Streeterville before heading out on a leisurely walk along the river, stopping along the way to practice restorative yoga poses while you take in unmissable sights. What better way to start your way in the city?
Another new addition in the Streeterville neighborhood, sample Chicago's signature dish (deep dish, to be more precise) with this three hour pizza tasting tour. Your expert food guide will show you around the city, stopping at four of Chicago's best pizzerias in search of the perfect slice.
| Thanks for reading!
Thanks for reading our Chicago neighborhood guide, updated for 2022!
Chicago is so much more than deep dish pizza and precise hot dog toppings (although those are both good, of course.) There’s a wealth of culture, history, and architecture to discover across a wide variety of friendly neighborhoods, from hidden gems off the beaten track to extravagant experiences popular with tourists and locals alike.
If it’s a unique gift idea you’re after or a once-in-a-lifetime Illinois vacation, you’ll find something for everyone in Chicago!
