Chicago Travel Guide 2021

2021 Chicago Visitors Guide

Big, bold, and relentlessly exciting, Chicago offers an endless array of cultural, recreational, and entertainment options for visitors to experience. The Windy City offers something for everyone to love, boasting everything from world-class museums to renowned restaurants to some of the nation’s finest theaters and parks. No matter what draws you to Chicago, you’re sure to have fun and an unforgettable time there.

The city boasts even more sights and attractions. Visitors can relax and have fun at Navy Pier, go shopping along the Magnificent Mile, explore historic neighborhoods like Old Town and Hyde Park, explore the beautiful Lincoln Park alongside the lakefront, and much more. The city’s collection of restaurants, shops, galleries, and nightclubs is nothing short of world-class as well.

Chicago Fun Guide

The Loop, the city’s densely-packed urban core, contains many of its iconic skyscrapers and top attractions to visit. Here, visitors will find the observation decks of two of the city’s tallest buildings, the Willis Tower and the John Hancock Center. Both observatories offer breathtaking views of the city’s famed skyline and Lake Michigan, making them must-see attractions for anyone traveling to the town. The Loop also plays host to Grant Park and Millennium Park, among the most beautiful urban parks in the United States. Both offer scenic views and are fantastic places to relax and unwind. The Loop also contains many of the city’s most renowned and famous theaters and entertainment complexes such as the historic Chicago Theater, the Auditorium Theatre, the Cadillac Palace Theater, and many more.

Chicago also hosts some of the world’s largest and most renowned museums, galleries and cultural institutions. The Art Institute of Chicago is the city’s flagship art museum and one of the most renowned art museums in the entire world. Nearby, the Museum Campus boasts three of the city’s top museums and cultural institutions; the Field Museum of Natural History, the Adler Planetarium, and the Shedd Aquarium, all of which are among the most respected science and natural history centers in the world. Other must-see museums in the city include the Clarke House Museum, the Museum of Contemporary Photography, the Museum of Contemporary Art, and much more.

A city that offers so much, Chicago is among the most popular destinations in the United States. From the soaring Willis Tower to the idyllic Lincoln Park, the renowned Art Institute of Chicago to historic Wrigley Field, this city offers a plethora of amazing attractions and fun things to do.

Chicago Downtown Hotels

The Downtown Chicago area, known to locals as “the Loop,” is a significant tourist draw. In addition to hosting some of the city’s most magnificent skyscrapers, the Loop is home to the important stages that comprise the Theater District. The Chicago Theatre, in particular, is one of the city’s most iconic cultural institutions. The Downtown area got its nickname because Chicago’s infamous “El” train makes a loop around the neighborhood. Here in the Loop, the average tourist is overwhelmed by the number of things to do and see. In addition to the city’s theater district, visitors can experience some of Chicago’s oldest eateries, its newer ones, and some of the best public art displays in the country. Tourists can glimpse Joan Miro’s “Moon, Sun and One Star” sculpture in a plaza near the Chicago Picasso, also known as the Chase Tower – a building that hosts Chagall’s “The Four Seasons” display.

Chicago Weather

Chicago has a reputation for changeable weather that can even become brutal at certain times of the year. Visitors to the city should be aware of the many faces of Chicago weather so they can have the appropriate clothing on hand when needed. Your careful preparation will make your visit more comfortable and enjoyable.

Chicago Springs

Spring in Chicago can bring any number of weather changes to the city. It’s best to be prepared for any eventuality by packing clothing that can be layered as needed. Temperatures at night can dip to 20 degrees Fahrenheit. Some spring days can be in the 60s, so be prepared for both extremes. Generally, temperatures are in the 30s or 40s from February onward, with gradual warming until it is in the 50s during April. May and early June can still be rainy and chilly. A jacket and raingear will be needed.

Summer in Chicago

Summer in Chicago can be glorious, with temperatures in the 80s, and rarely into the 90s. However, chilly days can occur when skies are overcast, and winds come off Lake Michigan. Keep a sweater on hand for sudden temperature drops and cooler night temperatures. Summer storms are frequent in Chicago, with rain, lightning, and thunder. Carry an umbrella to avoid getting soaked unexpectedly.

Autumn in Chicago

Autumn is one of the most beautiful times of the year in Chicago when the trees in the city itself and surrounding areas turn a variety of colors, making it the perfect background for travel photos. Though September days can retain some of the heat of summer, by mid-October, the weather turns. Bring a warm jacket for seeing the sights of the city, and an umbrella or raincoat to keep you dry, especially if you will be waiting outside for public transportation.

Chicago Winters

From late November, Chicago weather can become cold and unfriendly. Cold, damp rain and winds can chill people to the bone. A dense, windproof jacket and hat are necessary to keep out the chill. Light snow can fall on the city from late November and into December, making travel throughout the city more complicated. January is the coldest month in this northern metropolis. Temperatures can fall below zero with the wind chill factors making it dangerous to go out without having gloves, hats, and scarves to protect exposed skin. Though many people avoid visiting Chicago during these months, seeing the city during these periods is the only real way to understand the spirit and hardiness of this great American city.

Chicago Transportation

The Chicago Transit Authority manages city buses and trains running to and from 40 suburbs and within the heart of the Windy City. Buses and trains run several times per hour, and holiday routes apply to Thanksgiving, Christmas, New Year’s Day, Memorial Day, July 4th, and Labor Day. Some trains run on elevated tracks and are referred to as “the el.”

Buses accept cash fare or riders can purchase the Chicago Card or the Chicago Card Plus, which deducts the cost of the first ride, makes the first transfer a reduced rate, and makes the second transfer free. Reduced fares are also available to children, students, seniors, and those with disabilities. Cards can be purchased online through chicago-card.com, transitchicago.com, at rail stations, and certain grocery stores and pharmacies. The CTA sells 3-day and 7-day passes, which provide unlimited bus and train rides. METRA is the CTA’s sister agency, and it operates 11 commuter rail lines within Chicago to the suburbs.

Chicago has two international airports: O’Hare and Chicago Midway International Airport. The L train goes to both airports and saves riders money and time going from either airport to the downtown area. Taxis and shuttle van rides from O’Hare to downtown can take anywhere up to 90 minutes, and from Midway to downtown will take approximately 40 minutes; cab fare and shuttle van service will also cost significantly more than the train. On the other hand, the blue line L train route between downtown and directly into O’Hare’s lower level concourse takes approximately 45 minutes. This connects to terminals 1, 2, and 3, and another free shuttle train connects to terminal 5. The orange line L train between Midway and downtown takes about 25 minutes.

PACE is a bus transit system within the suburbs, and entirely of few of their routes connect with CTA routes, enabling those riders to travel into the city. Also, SOUTH SHORE LINE commuter trains run between Chicago’s downtown and Indiana’s South Bend Airport. Chicago’s taxis, although costing more than train and bus fare, are a great way to get around for short trips when you need door-to-door service.

A fun and unique way to see a different view of the city is on the Chicago River via the Chicago Water Taxi service, which has stops in Chinatown, Madison Street, LaSalle/Clark, and Michigan Avenue. Service runs seven days a week. Shoreline Sightseeing also operates water taxis around Navy Pier and to the Loop.

Chicago Attractions

Chicago, Illinois, is filled with amazing attractions. Navy Pier brings family and fun together. Take a ride on the Ferris wheel and take in the spectacular skyline of the city of Chicago. Afterward, bring the family to the Children’s Museum for a great time. Visit Millennium Park, where there are incredible state-of-the-art architecture, the famous Chicago Bean, and other fabulous works of art. Millennium Park is a sort of town square that hosts family activities such as a winter ice rink and flower fields. Millennium Park is perfect for a stroll and to host corporate and special events. Sports fans can catch a Cubs baseball game at Wrigley field while animal lovers can visit the Lincoln Park Zoo and the Brookfield Zoo. Art lovers will be pleasantly surprised by the many museums available in the Chicago area. There is the Gilmore Car Museum, the Volvo Auto Museum, the DuSable Museum, the Polish Museum of America, the Hyde Park Art Center, and the Field Museum of Natural History, to name a few.

Art Institute of Chicago

The Art Institute of Chicago is located in Grant Park and promotes art exhibits from Monet to Dali to contemporary artists. The Shedd Aquarium is also found in Grant Park and is an indoor public aquarium that is spectacular and has both freshwater and saltwater tanks. The Chicago River Architecture Tour is outstanding. Passengers will receive an architectural education while riding on the boat. The tour passes by the Civic Opera House, the Wrigley Building, and the famous Willis Tower (formerly known as Sears Tower), to name a few. The tour is remarkable and informative and is a must-see while in Chicago.

John Hancock Center

The John Hancock Center, located on the Gold Coast, has a beautiful observatory with a 360-degree view of the city of Chicago. John Hancock has plenty of shops and restaurants to enjoy as well. The Skydeck Chicago is also a popular attraction. The Skydeck (formerly the Sears Tower Skydeck) hosts breathtaking views from the tallest building in the western hemisphere.

Wright Home and Studio

The Wright Home and Studio is located in Oak Park and offers daily tours of the world-renowned architect Frank Lloyd Wright’s home and studio, including a walkthrough his former offices and drawing rooms. The Wright Robie House, located in Hyde Park, is another cultural experience that is not to be missed. The University of Chicago is another sight to behold with beautiful architecture and gorgeous grounds.

Chicago Dining

For many Chicagoans, eating and drinking isn’t just a way to stay alive, it’s a reason for living. People in Chicago love good food – be it the budget-friendly, down-home traditional favorites of burgers, hot dogs and pizza, unique offerings from around the world, classy downtown restaurants, or the high-end, experimental cuisine of the city’s best chefs.

Whether you are on a budget and want to eat and drink on cheap daily specials or whether you are ready to splurge on a meal you will never forget, there’s a restaurant in Chicago perfect for you. And though we love our meat, we also have a great selection of vegetarian and vegan restaurants.

We also love drinking almost as much as we love eating. That’s why we’re glad we have BYOB (bring your own beer or wine) restaurants, unique bars, all-you-can-drink mimosa brunches, and great nightlife. From speakeasy-style bars to swanky clubs to cheap dives to casual brewpubs and everything in between, there are hundreds of places in Chicago to wet your whistle with your favorite drink, even if you want to drink on a very small budget.

Giordano’s pizzeria

The wildly popular pizzeria, Giordano’s is undoubtedly a hot spot for locals and tourists, with many locations across the Chicago area. Here, you’ll find artfully crafted, over-sized pizzas sure to satisfy your appetite. Cheese-stuffed pizzas are Giordano’s specialty and the highest rated item among customers. They also offer thin-crusted pizzas, salads, sandwiches, flat-bread, and many appetizers. Giordano’s is also known for its nationwide shipping, making it easy for anyone across the U.S. to enjoy Giordano’s pizza. Many of Giordano’s locations are in the heart of the city, making it ideal for visiting tourists due to the proximity to various hotels, like the Omni Hotel, Park Hyatt, and the Allerton Hotel.

Yusho

A second must-see restaurant in Chicago is Yusho. Yusho caters to the Asian food lovers, showcasing numerous Japenese-oriented seafood dishes, foie gras, beef tongue, steamed buns with pork shoulder and kimchi, and more. Yusho also has unique dessert items, including mochi, ginger, or green tea tofu doughnuts, and soft serve. The spacious, homelike layout of the restaurant undoubtedly makes all patrons feel at home while enjoying delicious meals. There are many hotels located within walking distance, including the Wilshire and the Fullerton hotel.

Vera

Another phenomenal restaurant in Chicago is Vera. Vera is the ideal restaurant for any foodie because of its diverse menu and modern decor. Vera provides an extensive list of many small plates, known as tapas, that perfectly pair with their broad wine menu. There is an extensive range of options for each separate dish to accompany specific wines, including many goats and sheep cheese plates, various meat dishes like bacon, steak and duck, and many other snacks including marinated olives, spiced pecans, bread with olive oil and more. Vera is another beautiful restaurant that’s close to many hotels, including The Crowne Plaza Chicago Metro Hotel and the well-known Hotel Sax Chicago.

All of the fine dining establishments listed in this article are loved by locals. They are also perfect for traveling visitors who want to experience all the best cuisine in Chicago. Chicago is noted for having some of the best restaurants in the country, so there’s nothing that should stop you from planning your next culinary adventure.

 

Family Fun near Downtown Chicago

Chicago is a beautiful city for families to spend quality time together. Great for day trips or week-long vacations, Chicago offers a variety of attractions for people of all ages. If you’re a sports fanatic, cheer on one of Chicago’s many teams. A Cubs, White Sox, Bulls, Bears, or Blackhawks game is a great way to spend an afternoon of bonding.

For something more educational, stop by one of the many museums located in the heart of the city. The Field Museum is a wonderful way to learn new information. The Museum of Science and Industry is great for a hands-on experience. The Art Museum is a great place to go to gain insight into different forms of art. The Adler Planetarium is also a unique experience.

Shedd Aquarium

If you’re an animal lover, stop by the Shedd Aquarium and see hundreds of exhibits. Don’t miss the dolphin show, either! If it’s nice out, stop by the Lincoln Park Zoo and make friends with the animals.

John Hancock Observatory

Don’t forget about the more obvious attractions like the Willis Tower and the John Hancock Observatory. Both of these locations offer a view of the city and look even more incredible at night when the city is lit up. If you visit the Willis Tower, make sure to step out on the Skydeck; it’s an experience you won’t forget.

The Bean

If you’re looking for a cost-efficient way to relax, take a stroll on one of the paths along the lakefront. Chicago is known for its beautiful beaches, so spend a day soaking up the sun and enjoying each other’s company. For a more artsy adventure, spend a day picnicking by The Bean and look at all the unique architecture the city has to offer!

Navy Pier

Another excellent location for families to visit is Navy Pier. Full of small shops, dining, and a fun atmosphere, Navy Pier is a must-see. Navy Pier always has themed events going on which relate to the season. For additional fun, take a ride on the Ferris Wheel or visit the Children’s Museum.

Michigan Avenue

While all of these places are lovely options for families, don’t forget about shopping on Michigan Avenue! Chicago has hundreds of different stores and high-end brands to choose from.

Chicago is known for its cultural diversity. If you’re looking for a diverse dining experience, visit Chinatown or Greektown. If you’re looking to keep it traditional, make sure you bite into a Chicago-style hotdog or warm piece of cheesy pizza.

Shopping near Downtown Chicago

Chicago has long been a world premiere shopping and fashion destination for much of the century. Travelers and locals alike flock to the city of Chicago to find treasures in the many distinct shops and stores that are available. For excellence in shopping, look no further than Chicago’s Magnificent Mile located on Michigan Avenue.

Shopping Chicago’s Magnificent Mile

Chicago’s Magnificent Mile is home to boutiques, department stores, specialty retail shops, luxury stores, electronic stores, home furnishings, and high-end luxury stores. For apparel, there are stores such as Ann Taylor, Brooks Brothers, Juicy Couture, Cop-Copine Paris, Hugo Boss, Ralph Lauren, and Vince, to name a few. Department stores include Macy’s, Bloomingdales, Saks Fifth Avenue, Nordstrom, and Neiman Marcus. There are plenty of jewelry stores to choose from, including Cartier, David Yurman, Omega, Rolex, Tiffany and Company, and Trabert and Hoeffer, Inc. Home furnishing possibilities include Crate and Barrel, Pratesti, NEFF of Chicago, and Chiaroscuro. Electronic stores that are available include Apple, Best Buy, and Garm International. Toy shops are open and include American Girl Place, KOOKY, The Disney Store, and the Lego Store. Every shopper is sure to find the treasures they seek on the Magnificent Mile. Chicago’s Magnificent Mile is also home to large luxury stores that include well-known names such as Burberry, Escada, Giorgio Armani, Louis Vuitton, Prada, Paul Stuart, Salvadore Ferragamo, and Tumi.

Oak Street Shopping District

The abundant shopping continues in other parts of the city as well. Oak Street Shopping District has a collection of shopping malls and stores to choose from, including Tod’s, Kate Spade, and world-renowned Hermes. State Street in the heart of the Loop and offers stores and boutiques as well as discount stores such as Loehmanns, Nordstrom’s Rack, and Filene’s Basement. Neighborhood shopping is also available on Division Street and in the areas surrounding Lincoln Park and Lakeview. There is Point Zero as well as Jeweler’s Row available. Look for Armitage Avenue as well, which hosts Cynthia Rowley and Barker and Meowsky. West of Lakeview and just a few blocks from Wrigley Field is Southport Avenue, which hosts up and coming designers. Wicker Park and Bucktown offer shops and boutiques that are of the bohemian spirit.

Chicago is known as one of the world’s premier shopping destinations. The shops, boutiques, specialty stores, and department stores can be found all along the streets of the city. There is nothing that a traveler, tourist, or local cannot find on the Magnificent Mile and beyond.

Map of Hotels in Chicago

  1. Chicago Midway International Airport – Find hotels Near Summit and Bedford park city
  2. O’Hare International Airport – Find hotels near Quincy Bay & Winthrop
  3. Downtown Chicago – Find hotels near Chicago Opera House & Union Oyster House
  4. Millennium park – Find hotels near Spring Hill & Cambridge
  5. Navy Pier – Find hotels near Charlestown & Chicago Navy Yard
  6. Chicago Cultural Center – Find hotels near Chicago Common & Charlesbank Park
  7. Oak street beach – Find hotels near Union Oyster House & During Park
  8. University Village Little Italy – Find hotels near Peddocks Island & Hull Bay
  9. MJillers meadows forest preserve – Find hotels near Emmanuel College & Evans Way Park