Weekend in CHICAGO – INSIDER GUIDE (2020)

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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-renowned museums, and classic American cuisine. A weekend in Chicago will keep you busy, active & well fed!.

Chicago is home to some of the most iconic, and tallest buildings in the world! In fact, Chicago is actually the birthplace of the modern skyscraper which makes it an absolute must-visit city for any budding architects! 

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

This city on the shore is a great place to visit and definitely worth exploring on your next weekend break! Here are our top recommendations of the best things to do in Chicago this weekend!

 

Insider Tips for an AMAZING Weekend in Chicago

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

Insider Tips for an AMAZING Weekend in Chicago

Skyline Chicago

 

Know Where to Stay in Chicago

When choosing a place to stay in Chicago, do be mindful of its location as well as its amenities. To get around the city conveniently and to be nearby some iconic Chicago attractions, we recommend  downtown or in 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’s utterly central, houses Chicago’s most popular landmarks and is well connected by the city’s public transportation system; it’s the perfect base for spending 2 days in Chicago!

The Windy City is huge so and it can be a bit overwhelming trying to choose your accommodation. This is precisely why we have made this awesome guide to the best hostels in Chicago. Be sure to check it out for useful advice on where to stay in the city!

In case you are in a hurry though, here are three of the best accommodation options we recommend for a great weekend stay in Chicago!

 

Our Favorite Hostel – HI Chicago

HI Chicago

HI Chicago is our favorite hostel in Chicago!

  • Ideally located right in the city center
  • There are options for gender-separated dorms with en-suite bathrooms

This hostel is close to all of the city’s top tourist attractions, including art galleries, museums, shops and restaurants. It has over 500 comfortable beds, and offers free breakfast and walking tours throughout Chicago.

Check on HostelWorld

 

Our Favorite Airbnb – Modern loft for 2

Modern loft for 2, Chicago

Modern loft for 2 is our favorite Airbnb in Chicago!

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

Check on Airbnb

 

Our Favorite Budget Hotel – Freehand Chicago

Freehand Chicago

Freehand Chicago is our favorite budget hotel in Chicago!

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

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

Check on Booking.com

 

Our Favorite Splurge Hotel – Warwick Allerton Chicago

Warwick Allerton Chicago

Warwick Allerton Chicago is our favorite splurge hotel in Chicago!

  • Simple and elegant decor 
  • Enjoy magnificent views over the Chicago River and Lake Michigan

Located in the heart of Downtown Chicago, this luxury hotel towers above the city and offers upscale amenities and stylish comfort. There is an on-site bar, restaurant, and fitness center. 

Check on Booking.com

 

Know How to Get Around in Chicago

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

However,  Chicago is a big city that’s spread out over a large area so walking between the various neighbourhoods can be very time consuming. 

For moving between Chicago’s neighbourhoods, there is a vast network of public transport 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 the train stops to most Chicago points of interest. 

If you don’t fancy  spending time on the public transport system, then bicycles are a great option! There are a few bike rentals in Chicago as well as the city’s bike-sharing system known as “Divvy Bikes” with bases around the metro stations 

The Divvy bikes are an easy and affordable way to get around, especially over a weekend in Chicago!

 

Chicago Nightlife Guide

chicago at night

source: rickveldman (Pixabay)

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

 

River North

  • 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 hit up Hubbard Street to experience an authentic Chicago Saturday night!

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

 

Wrigleyville

  • For a unique Chicago experience head to Clark Street and catch a Cubs game 
  • Cubs fans fill up 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 watering holes; it may even be the longest cluster 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!

 

Wicker Park

  • Head to North Milwaukee Avenue and you’ll find an eclectic mix of bars, pubs and clubs 
  • Some of the more popular spots include Whiskey Business, SWIG and Debonair
  • Around Logan Square, just a few blocks up Milwaukee, is another small cluster of bars with good vibes 

Wicker Park provides a more alternative scene in Chicago. The main artery is North Milwaukee Avenue. You’ll find a funky mix of pubs, clubs and bars that attracts a colorful bunch of party-goers! While this area is well serviced with public transport, it may be a good idea to catch a taxi when returning home.

The Best Travel Backpack?!

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Read our full review!

 

Chicago Food Guide

Chicago food

Chicago has a delicious food scene!

If you’re a fan of pizza, then you must try the famous Chicago-style deep dish pizza which is now a hit across the US! The Chicago-style hot dog is another dish Chicagoans take great pride in. 

Here are some stellar recommendations for where to eat in Chicago.

Lou Malnati’s Pizzeria

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

Widely regarded by locals as the best place to get a deep-dish pizza, Lou Malnati’s is one of Chicago’s best-known pizza chains! It is, therefore, no surprise to learn that it was founded by the son of Rudy Malnati, the guy who helped developed the recipe for Chicago-style pizza!

 

Gene & Jude’s

  • Well-known for serving the best Chicago-style hot dogs in the city! 
  • This popular food stand is packed with customers all day long
  • Each hot dog is served 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’s make them best! The true Chicago dog comprises a Vienna sausage in a poppy seed bun with mustard, relish, chopped onions, hot peppers, tomatoes, dill pickles and a dash of celery salt. You won’t find ketchup anywhere on-site!

 

Take a Food Tour in 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 spots, including Millennium Park, Palmer House Hotel, the Art Institute and the Bean
  • 2.5-hour food themed walking tour through the streets of Chicago

For a comprehensive understanding of the city’s cuisine, take a food walking tour and taste all the iconic dishes that have come out of Chicago! This tour combines an enjoyable walk around Chicago’s Downtown area with plenty of stops to sample some of the city’s famous tastes!

 

Sporting Events in Chicago

Chicago sports

Chicago has some really cool experiences for sports lovers!

Sport is definitely one of the Chicago highlights and you can get out and be active no matter the season! Whether you prefer taking part in an activity, or just watching, there are always plenty of options on offer!

 

Wrigley Field

  • First opened in 1914, this is one of America’s most iconic baseball parks 
  • Home of Major League Baseball team the Chicago Cubs
  • Known for its ivy covered home-run wall, it’s the second oldest stadium in MLB!

If your weekend getaway to Chicago coincides with a baseball game, do your best to rustle  up some tickets and soak in the festive atmosphere of America’s favorite pass time! 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 going! 
  • Choose between a range of heart-pumping driving experiences
  • Set your fastest lap on a real NASCAR speedway!

If your racing addiction demands more than just a seat on the sidelines, check out Chicagoland Speedway! This fun location offer exciting options that will definitely satisfy your need for speed! Get behind the wheel of a NASCAR and take it for a spin on Chicago’s NASCAR speedway!

 

Fame Play Ping Pong at Acebounce

  • Challenge your friends to a game, or three of ping-pong
  • Work up a thirst, then enjoy some drinks from the on-site bar
  • A great social source of fun on a weekend trip to Chicago!

If you’re looking for an indoors activity in Chicago, look no further than Acebounce where you can enjoy games of ping-pong, or beer pong! Sink a few pints and dance to the beat from live DJ’s! This is a fun way to spend a chilled-out Sunday in Chicago. 

Gardens Neighborhood, Cape Town

You should always have emergency cash hidden on you – pick up this awesome security belt with its hidden pocket before you travel, it’s perfect for hiding money, a passport photocopy.

GET IT HERE

 

Weekend Cultural Entertainment in Chicago – Music/Concerts/Theatre

Chicago entertainment

There are plenty of shows and events in Chicago!

Your Chicago itinerary should include some nocturnal fun and the city has plenty of great music and theatre options. Here are three of Chicago’s best venues for entertainment!

 

Green Mill Jazz Club

  • A great venue 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 during the 1920s

Green Mill Jazz Club in Uptown Chicago is a former speak-easy dating back to 1907. It’s the longest continuously running jazz club in the country! Slip into one of the glamorous curved booths and listen sultry singers, big band and bebop! This is one of the most entertaining things going on in Chicago this weekend! 

 

The Hideout

  • A great place to go for live music on a Saturday in Chicago 
  • An intimate prohibition-era bar that host all sorts of live music and dancing 
  • Check out their line-up on their calendar page

This beloved Chicago hangout has a bar in the front and a stage in the back. It offers a cozy vibe and casual aesthetic. After you find the obscure industrial side-street it’s hidden on, you’ll join a welcoming crowd. The outside 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 superb venue!
  • A lively atmosphere that lends itself well to enjoying live music
  • Food is also available at their restaurant 

This mainstream jazz club runs regular, low-key residencies with some of Chicago’s most respected jazz musicians! There are regular performances that showcase the local jazz talent. This venue is a comfortable, intimate space where you can drop by for a cocktail and a bite to eat. Andy’s is sure to draw a crowd any day of the week, especially in Chicago on Sundays! 

 

10 Other Awesome Things to do in Chicago This Weekend

So, you’re still looking for more fun things to do in Chicago? Need more Chicago weekend events and attractions? Not to worry, we’ve got you covered!

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

 

#1 – Get Up Close to the Aquatic Wildlife of Shedd Aquarium

Get Up Close to the Aquatic Wildlife of Shedd Aquarium

Source: Smart Destinations (Flickr)

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

There are freshwater displays with 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-do Chicago weekend activities with kids!

 

#2 – Stop in at the Field Museum

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

Founded with an endowment from Marshall Field, it has since gone on to house one of the finest collections of artefacts in the United States. Everything from precious gems to a Tyrannosaurus-Rex skeleton are found here.

Permanent exhibits range from animal dioramas to interactive displays that engage all ages. There are also cultural displays, walk-throughs detailing the planet’s evolutionary processes, and exhibits delving into cellular-level research and technology!

 

#3 – Stand Above the City Skyline at Chicago Sky-deck

Stand Above the City Skyline at Chicago Sky deck

Source: Mariusz S. Jurgielewicz (Shutterstock)

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

There are windows on all sides of the observatory that offer unparalleled panoramic views of the surrounding city, and beyond! There’s also an all-glass enclosure that looks straight down onto the busy streets of Chicago! Enjoy a movie detailing the 45-year history of the Willis Tower and Chicago’s other architectural wonders.

 

#4 – Go Shopping Along the Magnificent Mile

The Magnificent Mile is a row of exclusive shops, department stores and boutiques that line the northern half of Michigan Avenue. If you’re spending 3 days in Chicago, make sure to visit one of the best shopping districts in town!

Originally designed by 19th-century architect Daniel Burnham, this famous section of Michigan Avenue has a plush assortment of historic buildings in various architectural styles. Among its jewels are the Tribune Tower, the Wrigley Building, the John Hancock Center, the Drake Hotel, and the Historic Water Tower; one of the few structures that survived the Great Fire of Chicago.

HI Chicago

Check Best Price

 
HI Chicago
This hostel is close to all of the city’s top tourist attractions, including art galleries, museums, shops and restaurants.
 
 
  • Free WiFi
  • Free Breakfast
  • 24 Hour Reception

 

#5 – Admire the Grand Works of the Art Institute of Chicago

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

The museum has an incredible collection of French Impressionist paintings and other artworks 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. 

Some of the most famous pieces include Chagall’s America Windows, Matisse’s Bathers by the River, and Georgia O’Keeffe’s Black Cross, New Mexico.

 

#6 – Check Out Wild Animals at Lincoln Park Zoo

Check Out Wild Animals at Lincoln Park Zoo

Source: alisafarov (Shutterstock)

Lincoln Park Zoo is one of the oldest zoos in the United States, and it’s completely free to the public! This makes it one of the best free things to do in Chicago this weekend! 

Explore the Reptile House and see all things that slither, or head over to the outdoor exhibits and watch the polar bears swimming in their pool! Check out the Waterfowl Lagoon to see water-dwelling birds in an open habitat, or stop at the Lion House and watch a pride of big cats enjoying their day!

 

#7 – Visit Navy Pier

Navy Pier

Navy Pier

Navy Pier extends out into Lake Michigan at the mouth of the Chicago River. It boasts a newly-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, numerous eating options, and live concerts! Stroll around the pier to enjoy everything it has to offer, or take a Chicago river cruise on one of the many boat tour companies that moor at the pier during the warmer months.

 

#8 – Take an Architectural River Cruise

Architectural River Cruise

Architectural River Cruise

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

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

 

#9 – Visit the Museum of Science and Industry

The Museum of Science and Industry is located in Hyde Park which is a little bit further out from 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 artefacts and displays, including Colleen Moore’s Fairy Tale Dollhouse, made from precious gems and materials. Also on display is a WWII German submarine and a Pioneer locomotive. Definitely go check it out if you have extra time on your weekend trip to Chicago!

 

#10 – Snap a Photo at the Cloud Gate Sculpture at Millennium Park

Don’t miss a chance 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 finish creates fascinating reflections and captivates everyone that passes by!

This famous Chicago landmark is an absolute must-see when visiting! This park is also home to a two glass tower fountain. The tower fountains have faces projected onto them to make them look as if their mouths are streaming water into the pool!

Don’t forget to pack a good book!

Chicago: A Novel: This is our top recommendation for an awesome and inspiring read on this magical city.

 

Chicago Weekend Travel FAQs

Chicago Weekend Travel FAQs

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

 

#1. What should I pack for a weekend in Chicago?

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

  • As many of Chicago’s points of interest are concentrated in a few suburbs, it’s often best to walk between them. Therefore make sure to pack some comfortable walking shoes with support! Don’t forget to also pack some formal shoes if you plan on hitting up a jazz lounge or two!
  • Chicago’s weather can get pretty extreme rangingfrom howling blizzards in winter to steamingly humid days in summer! Make sure you pack some layered clothing, and be prepared to expect the unexpected any time of the year! Even in summer, the night time temperatures can get a bit chilly.  
  • Pack a reusable water bottle to keep 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. Not only will you be saving money, you’ll also be doing your part to save the environment!

#2. Can I get an apartment in Chicago for the weekend?

Most definitely! Airbnb is the perfect option for booking your accommodation in Chicago. You can easily filter whatever amenities you prefer (kitchen, parking on site, TV, etc) and enjoy all the luxuries of having your own place for the weekend!

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

Staying in an Airbnb also comes with the added bonus of being able to stay with a local. There are plenty of friendly hosts who are willing to provide visitors with insider-tips and useful insight on how to make the most of a two-day stay in Chicago! 

Booking.com also has apartment listings on their website to choose from, and often in premier locations. A perk to this is that you go through a company for booking accommodation, and not a private individual. 

 

#3. Is Chicago safe for a weekend trip?

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

Chicago does experience violence and crime, but this is predominantly confined to specific hotspots, such as the far West Side of Chicago and the South Side of Chicago. While these areas are clearly dodgy, and gang violence and crime does occur, they are well away from Downtown Chicago. 

Be aware of your possessions when in crowds or around busy areas as pickpockets do frequent popular sights in the city. At night, it is best to keep to well-lit streets and populated areas as muggings do occur in dark side streets after dark.

Be sure to check the weather forecast for potential natural hazards, which can occur during the particularly harsh Chicago Winter.

Don’t forget to sort your travel insurance! We’ve put together a roundup of the best travel insurance for travelers, or if you’re low on time, get a quote from World Nomads now, our favourite travel insurance provider.

world nomads insurance banner

 

Final Thoughts on a Great Weekend in Chicago

Now that you have the best information on what to do in Chicago this weekend, all that’s left to do is pick the weekend that suits you and enjoy an incredible Chicago trip! Check out our backpacking Chicago travel guide for even more tips on saving money when visiting Chicago.

This city has a rich history, vibrant music scene, impressive architecture, and delicious food! There’s an array of impressive sights dotted throughout the city, and although it’s a large city, getting around without a car should be pretty easy!

Be sure to take in all the quirkiness and nuances that the Windy City has to offer! It’s possible to see a lot of Chicago in 3 days if you plan correctly, but if you decide to stay longer, check out our full Chicago itinerary.

 

Yay for transparency! Some of the links in this post are affiliate links. This means that if you book your accommodation through the site, The Broke Backpacker will earn a small commission at no extra cost to you. Your support helps me keep the site going.


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