How to spend the PERFECT weekend in Chicago (GUIDE 2022)

Chicago is one of the largest cities in the United States.Located on Lake Michigan in Illinois, the "Windy City" is famous for its bold architecture, world-famous museums and classic American cuisine.A weekend in Chicago will keep you busy, active and satiated!.

Chicago is home to some of the most famous and tallest buildings in the world!In fact, Chicago is the birthplace of the modern skyscraper, making it a must-see for any budding architect!

The city is also filled with some of the best museums in the country, ranging from amazing art museums to fully interactive science museums.

This coastal city is a great place to visit and definitely worth checking out on your next weekend getaway!Here are our top recommendations for the best things to do in Chicago this weekend!

Insider tips for an AWESOME weekend in Chicago

A weekend trip to Chicago is plenty of time to explore the city, and you can easily see a lot of.Check out our top tips for getting the most out of your stay in the Windy City!

With a Chicago City Pass, you can experience the best of Chicago at the LOWEST prices.Discounts, attractions, tickets, and even public transportation come standard with a good City Pass – invest now and save $$$ when you arrive!

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Know where to stay in Chicago

When choosing a place to stay in Chicago, look for both location and amenities.To get around the city comfortably and be close to some of Chicago's famous attractions, we recommend downtown or a central location.

Downtown Chicago (known locally as The Loop) is one of the best places to stay in Chicago for first-time visitors!It is absolutely central, hosts Chicago's most popular attractions and is well connected to the city's public transportation system. It's the perfect base to spend 2 days in Chicago!

The Windy City is huge and it can be a bit overwhelming when you're trying to choose your accommodations.However, if you're in a hurry, here are three of the best lodging options we recommend for a great weekend stay in Chicago!

Our favorite hostel – HI Chicago

  • Ideally located directly in the city center
  • There are options for gender-separated dorms with private bathrooms

This hostel is close to all of the city's major tourist attractions, including art galleries, museums, stores and restaurants.It has more than 500 comfortable beds and offers free breakfast and walking tours throughout Chicago.

Our favorite Airbnb – Artistic apartment with funky vibes

With this simple, practical and affordable studio apartment, you'll have access to a comfortable queen-size bed, a fully equipped kitchen, on-site laundry, free Wi-Fi and a great host who will recommend places to visit and things to do in Chicago.

Our favorite budget hotel – Freehand Chicago

  • Located in the heart of Chicago!
  • Just a short walk from the Magnificent Mile!

Housed in a classic 1920s building, the Freehand Chicago is a charming and stylish hotel.The decor has an industrial modern theme.In addition to the usual hotel amenities, there's also a cocktail bar, fitness room, and laundry facilities.

Check out our EPIC lodging guides for Chicago and book your stay!

Know how to get around Chicago

Walking is a great way to explore Chicago, and many of the best attractions are conveniently located in the central downtown area.Most Airbnbs in Chicago are also centrally located.

Chicago is a big city, however, and it covers a lot of territory, so walking between neighborhoods can be time-consuming.

To get around between Chicago neighborhoods, there's a huge network of public transportation options.The L train has stations all over Chicago and is a great way to explore the city!There is also an army of efficient buses that connect train stops to most Chicago attractions.

If you don't want to spend time on public transportation, bikes are a good option!There are a few bike rentals in Chicago, as well as the city's bike rental system known as Divvy Bikes, which has bases near subway stations

Divvy bikes are an easy and affordable way to get around, especially on a weekend in Chicago.It's also probably one of the most fun you can have when visiting Chicago!

Chicago Nightlife Guide

Most downtown Chicago hotels have some sort of bar attached, making it an easy choice for a quick drink.If you want to experience the authentic Chicago nightlife atmosphere, it's best to venture out to the suburbs.Here are three great options for a good night out!

North River

  • Close to downtown and well connected by public transportation
  • The most popular bars in the area are El Hefe, Howl at the Moon and Mother Hubbard's
  • Be sure to visit Hubbard Street to experience an authentic Saturday night in Chicago!

Head to Hubbard Street in River North for a wild night out!Whether it's during the week or on the weekend, the bars in this area are bustling with activity!This is Chicago's best nightlife district and attracts just about everyone!It's also the best area in the city to go bar hopping with friends!


  • For a unique Chicago experience, visit Clark Street and catch a Cubs game
  • Cubs fans fill most bars and it can get rowdy!
  • Irish Oak, Deuces and the Diamond Club and Sluggers are three great options!

Head to Clark Street in Wrigleyville and experience the nightlife with the locals!This long street is full of bars and pubs; In fact, it may be the longest collection of bars in the city!The energy is especially high during Cubs games and Saturday nights.This area attracts a slightly younger crowd and the bars can get festive!

Willow Park

  • Walk to North Milwaukee Avenue and you'll find an eclectic mix of bars, pubs and clubs
  • Some of the most popular spots include Whiskey Business, SWIG and Debonair
  • Around Logan Square, just a few blocks down Milwaukee, there's another small collection of bars with good vibes

Wicker Park offers a more alternative scene for people looking for more unusual activities in Chicago.The main thoroughfare is North Milwaukee Avenue.A funky mix of pubs, clubs and bars awaits here, attracting plenty of partygoers!Although this area is well served by public transportation, it may be a good idea to take a cab when you return home.

Chicago Food Guide

If you are a fan of pizza, then you must try the famous Chicago-style Deep Dish Pizza, which is now a hit in the U.S!The Chicago-style hot dog is another dish Chicagoans are very proud of.

Here are some great recommendations for restaurants in Chicago.

Lou Malnati's Pizzeria

  • You'll find this popular pizza chain in almost every Chicago neighborhood!
  • Order online and have your food delivered, or sit down and eat at the restaurant
  • Don't leave Chicago without trying some of their world famous pizzas!

Widely regarded by locals as the best place to get a deep-dish pizza, Lou Malnati's is one of Chicago's most well-known pizza chains!So it's no surprise to learn that it was founded by the son of Rudy Malnati, the man who helped develop the recipe for Chicago-style pizza!

Gene & Judes

  • Known for serving the best Chicago-style hot dogs in the city!
  • This popular food stand is packed with customers all day long
  • Every hot dog comes with fries, whether you like it or not!

Another icon of the city is the Chicago Hot Dog, and it's no secret that Gene & Jude make them the best!The true Chicago Dog consists of a Vienna sausage in a poppy seed bun with mustard, relish, chopped onions, hot peppers, tomatoes, dill pickles and a pinch of celery salt.You won't find ketchup anywhere locally!

Take a food tour around the city

  • Enjoy deep-dish pizza, the original brownie, a Chicago-style hot dog and local craft beer!
  • See some of Chicago's most famous sites, including Millennium Park, the Palmer House Hotel, the Art Institute and The Bean
  • 2.5-hour food-themed walking tour through the streets of Chicago

For a full understanding of the city's cuisine, take a food walking tour and sample all the iconic dishes that originated in Chicago!This tour combines a pleasant stroll through downtown Chicago with plenty of stops to sample some of the city's famous flavors!

Sporting events in Chicago

Sports are definitely one of the highlights of Chicago and you can get out and be active any time of the year!Whether you'd rather participate in an activity or just watch, there are always plenty of options!

Wrigley Field

  • First opened in 1914, this is one of America's most famous baseball parks
  • Home of the major league baseball team, the Chicago Cubs
  • It's MLB's second-oldest stadium, known for its ivy-covered home run wall!

If your weekend trip to Chicago coincides with a baseball game, do your best to get some tickets and enjoy the festive atmosphere of America's most popular pastime!Wrigley Field baseball stadium is located on the north side of Chicago and is easily accessible by public transportation.

Chicagoland Speedway

  • Head to Chicagoland Speedway to test your high-speed driving skills and get your adrenaline pumping!
  • Choose from a range of breathtaking driving experiences
  • Drive your fastest lap on a real NASCAR speedway!

If your racing cravings require more than a seat on the sidelines, check out Chicagoland Speedway!This fun place offers exciting opportunities that will definitely satisfy your need for speed!Get behind the wheel of a NASCAR and take a lap around Chicago's NASCAR Speedway!

Glory Play Ping Pong at Acebounce

  • Challenge your friends to a game or three of ping pong
  • Quench your thirst and then enjoy a few drinks from the in-house bar
  • A great source of social fun on a weekend trip to Chicago!

If you're looking for an indoor activity in Chicago, Acebounce is the place to be, where you can play ping pong or beer pong!Drink a few pints and dance to the beat of live DJs!This is a fun way to spend a relaxing Sunday in Chicago.

Cultural entertainment on weekends in Chicago – music/concerts/theater

Your Chicago itinerary should include some nighttime fun, and the city has many great music and theater options.Here are three of Chicago's best entertainment venues!

Green Mill Jazz Club

  • A great place to listen to jazz all night long
  • Arrive early, grab a cocktail and settle in for a relaxing evening of free jazz and bebop!
  • This was a local hangout for Al Capone and other gangsters in the 1920s

The Green Mill Jazz Club in Uptown Chicago is a former speakeasy that dates back to 1907.It's the longest continuously operating jazz club in the country!Slip into one of the glamorous curved booths and listen to sultry singers, big band and bebop!This is one of the most fun things to do in Chicago this weekend!

The Hideaway

  • A great place for live music on a Saturday in Chicago
  • An intimate Prohibition-era bar that hosts all kinds of live music and dancing
  • Check out their lineup on their calendar page

This popular Chicago hangout has a bar in front and a stage in back.It offers a cozy atmosphere and casual aesthetic.After you find the obscure industrial side street where it's tucked away, join a welcoming crowd.The outdoor patio is also used for eclectic music sets, weekly bingo, and comedy and dance nights!

Andy's Jazz Club & Restaurant

  • Enjoy live jazz music 7 nights a week at this outstanding venue!
  • A lively atmosphere that's great for enjoying live music
  • Food is also available at their restaurant

This mainstream jazz club offers regular, low-key residencies with some of Chicago's most respected jazz musicians!There are regular performances that showcase local jazz talent.This place is a comfortable, intimate spot where you can stop by for a cocktail and a bite to eat.Andy's draws a crowd any day of the week, especially on Sundays in Chicago!

10 more great things to do in Chicago this weekend

So you're looking for more fun things to do on your trip to Chicago?Need more weekend events and attractions in Chicago?Don't worry, we are here for you!

Here are 10 more activities, attractions and events in Chicago this weekend!

#1 – Get up close and personal with aquatic wildlife at the Shedd Aquarium

Located on the Museum Campus of Chicago along with the Field Museum and Adler Planetarium, the Shedd Aquarium was once the largest indoor aquarium in the world.This attraction has an incredible variety of aquatic wildlife from around the world!

There are freshwater exhibits featuring Amazonian animals, oceanic reefs with sharks, tropical fish and corals, touch zones, marine mammals and a plethora of other sea creatures!The aquarium is interactive and educational, it's definitely a must for weekend activities with kids in Chicago!

#2 – Stop by the Field Museum

The Field Museum is Chicago's premier natural history museum and one of the largest of its kind in the world!

It was established with an endowment from Marshall Field and has since housed one of the finest collections of artifacts in the United States.Everything from precious gems to a tyrannosaurus rex skeleton can be found here.

The permanent exhibits range from animal dioramas to interactive displays that appeal to all ages.There are also cultural exhibits, tours that describe the planet's evolutionary processes, and exhibits that deal with research and technology at the cellular level!

#3 – Stand above the city skyline on the Chicago Sky Deck

SkyDeck Chicago is located at the very top of Willis Tower, one of the tallest buildings in the world!After a short ride up, you'll be amazed at the sheer height of the observation deck and how far you can see beyond the city!

Windows on all sides of the observatory offer unparalleled panoramic views of the surrounding city and beyond!There is also an all-glass enclosure that looks directly onto the bustling streets of Chicago!Enjoy a film chronicling the 45-year history of Willis Tower and Chicago's other architectural wonders.

#4 – Go shopping along the Magnificent Mile

The Magnificent Mile is a series of exclusive stores, department stores and boutiques that line the northern half of Michigan Avenue.If you spend 3 days in Chicago, be sure to visit one of the city's best shopping districts!

This famous stretch of Michigan Avenue, originally designed by 19th-century architect Daniel Burnham. The city, which was designed in the nineteenth century, offers a magnificent array of historic buildings in a variety of architectural styles.Its jewels include Tribune Tower, the Wrigley Building, the John Hancock Center, the Drake Hotel and the Historic Water Tower; one of the few structures to survive the Great Chicago Fire.


HELLO Chicago

This hostel is close to all of the city's major tourist attractions, including art galleries, museums, stores and restaurants.

#5 – Admire the great works of the Art Institute of Chicago

The Art Institute of Chicago is located in the center of Grant Park on Michigan Avenue.It is the second largest art museum in the country and everything about this art institute is impressive!Most notable are the two famous lion statues created by Edward Kennys for the museum's opening in 1893.

The museum has an incredible collection of French Impressionist paintings and other artwork from around the world!A visit to this museum is a must for art lovers, who will especially enjoy this addition to their Chicago itinerary.

Among its most famous pieces are Chagall'sAmerica Windows, Matisse's Bathers by the River and Georgia O'Keeffe's Black Cross, New Mexico.

#6 – See Wild Animals at Lincoln Park Zoo

Navy Pier stretches from the mouth of the Chicago River into Lake Michigan.It features a redesigned Ferris wheel called the Centennial Wheel, as well as a handful of other amusement park rides.

The pier is also home to the Children's Museum, Chicago Shakespeare Theater, weekly fireworks shows, numerous dining options and live concerts!Stroll around the pier to enjoy all it has to offer, or take a Chicago river cruise with one of the many boat tour companies that moor at the pier in the warmer months.

#8 – Take an architectural river cruise

A Chicago architecture river cruise is a great way to see Chicago's amazing architecture from the water!Architecture and building design play a large role in Chicago's culture.Many of the world's most famous architects hail from Chicago, and some of the most famous buildings are part of its skyline.

Take a boat ride and admire some of the most famous and unique buildings along the river.Learn about the history and creation of more than 50 skyscrapers in Chicago.This cruise is one of the coolest things to do this weekend in Chicago!

If you're looking for a more memorable way to see the river and Lake Michigan, consider renting a boat in Chicago that will take you and your group anywhere you want to go!

#9 – Visit the Museum of Science and Industry

The Museum of Science and Industry is located in Hyde Park, a little further out of the city center, but absolutely worth the trip!This museum was part of the Columbian Exposition of 1893.

The institution's collection includes many unique artifacts and exhibits, including Colleen Moore'sFairytale dollhouse made of precious gems and materials.Also on display are a World War II German submarine and a Pioneer locomotive.Be sure to check it out if you have extra time on your weekend trip to Chicago!

#10 – Take a photo at the Cloud Gate sculpture in Millennium Park

Don't miss the opportunity to visit Cloud Gate, the famous sculpture by Anish Kapoor.This attraction is located in Millennium Park, at the north end of Grant Park.Also known as "The Bean," its curved, mirrored surface creates mesmerizing reflections and captivates everyone who passes by!

This famous Chicago landmark is a must-see during a visit!This park is also home to a fountain with two glass towers.The tower fountains have faces projected onto them to make them look like their mouths are pouring water into the pool!

Frequently Asked Questions About Chicago Weekend Trips

Even a weekend getaway requires some research to get the most out of your visit.To keep this research time to a minimum for you, we've compiled some of the most frequently asked questions about a weekend trip to Chicago!

What to pack for a weekend in Chicago?

In addition to the essentials, here are a few things we recommend you pack before you head out for your Chicago weekend.

– Since many of Chicago's landmarks are concentrated in a few suburbs, it's often best to walk between them.So be sure to pack comfortable walking shoes with support!Don't forget to pack formal shoes, too, if you plan to visit a jazz lounge or two!

– Chicago weather can get pretty extreme, from howling snowstorms in the winter to steamy humid days in the summer!Make sure to pack layered clothing, and be prepared to expect the unexpected at any time of year!Nighttime temperatures can get a bit chilly in the summer, too.

– Pack a usable water bottle to stay hydrated if you plan on walking around a lot.There are many water fountains in the city where you can fill up, so there is little need to buy bottled water.Here's how to not only save money, but also do something for the environment!

Can I get a place to stay in Chicago for the weekend?

For sure!Airbnb is the perfect option for booking your Chicago accommodation.You can easily filter the amenities you prefer (kitchen, onsite parking, television, etc.) and enjoy all the luxury of having your own home for the weekend!

This is a great money saving option for larger groups, as you can find larger accommodations and split the cost without having to pay for separate hotel rooms!

Staying in an Airbnb also has the added benefit of being able to stay overnight with a local resident.There are plenty of friendly hosts ready to give visitors insider tips and useful insights on how to make the most of a two-day stay in Chicago! also has apartment listings on their website to choose from, and often in prime locations.One advantage to this is that you are booking accommodations through a company rather than a private individual.

Is Chicago safe for a weekend getaway?

Chicago is largely a safe city, and tourists shouldn't have to worry too much when walking around downtown or visiting well-known landmarks.However, it's always a good idea to do some research or ask locals before venturing into the peripheral neighborhoods of the city.

There is violence and crime in Chicago, but this is mainly limited to certain hotspots like the far west side of Chicago and the south side of Chicago.Although these neighborhoods are definitely seedy and gang violence and crime occur, they are far from downtown Chicago.

Watch your belongings in crowds or busy areas, as pickpockets often target popular sights in the city.At night, it's best to stick to well-lit streets and populated areas, as dark side streets are prone to muggings after dark.

Be sure to check the weather forecast for potential natural hazards that may occur during Chicago's particularly harsh winter.

Don't forget your Chicago travel insurance

It's good to get lost sometimes, but it's also good not to get too lost.There are people who want you to come home in one piece.

There's one travel insurance provider The Broke Backpacker trusts with all its wildest shenanigans … World Nomads!

Click the button below to get a quote for your insurance, or read our in-depth review of coverage from World Nomads.And then… let the shenanigans begin. 😉

Final thoughts on a great weekend in Chicago

Now that you have the best information on what to do in Chicago this weekend, all you have to do is pick the weekend that suits you and enjoy an incredible Chicago trip!

This city has a rich history, a vibrant music scene, stunning architecture, and delicious food!There are a number of impressive sights throughout the city, and even though it's a big city, it should be pretty easy to get around without a car!

Be sure to take in all the quirkiness and nuance the Windy City has to offer!It is possible to see a lot of Chicago in 3 days if you plan properly.

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