12 Best Hotels in Chicago, United States - May 2019

The metropolis of Chicago has a rich history, with many cultural attractions that date back over a century. It also has an exquisite skyline, hosting some of the tallest buildings in the United States--and in the Western Hemisphere! When in Chicago, you have easy access to the nearby states as well: Michigan, Wisconsin, and Indiana. So a trip to Chicago can let you take in a good part of the American Midwest!

What are the Must-Do-s and See-s in Chicago?

The Chicago Loop

“The Loop” is the name for Chicago’s downtown area, including its business district and City Hall. Besides Willis Tower (that we discuss below), other Chicago tourist attractions are also located here--the Chicago Board of Trade Building, the Chicago Symphony Orchestra, the Lyric Opera of Chicago, the Art Institute of Chicago, and more.

Willis Tower (Formerly known as the Sears Tower)

Chicago’s Willis Tower is a 110-story skyscraper that was constructed from 1970-1973. For many years, it was crowned the tallest building in the United States. In 2009, they added the Skydeck observation deck on the 103rd floor, and The Ledge--an enclosed glass box that extends 4.3 feet out over the Skydeck. Not only can you see out to Indiana, Wisconsin, and Michigan--you can get a exhilarating view of the street below! There are interactive exhibits and even games at the observation deck as well.

Grant Park--Millennium Park--Maggie Daley Park

On the section of Chicago along Lake Michigan, there are several attractive parks. The northernmost is Millennium Park, with “The Bean”--a stainless steel statue named “Cloud Gate” by the artist Sir Anish Kapoor. The metal is polished so that it reflects Chicago’s skyline. There are always tourists taking selfies with the impressive work of art. There is also the McCormick Tribune Plaza and Ice Skating Rink nearby, and the Jay Pritzker Pavilion, which hosts performances in the summertime. The Crown Fountain is another interesting piece of artwork in the park: It is two rectangular-shaped fountains facing each other, with each fountain containing a LED screen and a digital video of a person’s face--usually of one of the park goers. Nearby, you’ll also find Maggie Daley Park and Grant Park, with lots of activities for children, and the Art Institute of Chicago, dating from 1879, and housing more than 300,000 works of art! Grant Park also has the Shedd Aquarium, Adler Planetarium, and the Field Science Museum. The Palmer House Hilton is a nice hotel in the area.

Magnificent Mile

Magnificent Mile is a mile-long stretch near downtown Chicago, north of Millenium Park and across the Chicago River. Notable sites in the Magnificent Mile include the Michigan Avenue Shopping Center, which is a series of three vertical shopping malls: 900 North Michigan Shops, Water Tower Place, and The Shops at North Bridge.

Chicago was always known for its architecture--and some distinct structures include the Tribune Tower, which has specimens of landmarks from around the world worked into its walls. Check out the unique Aqua skyscraper, with its wavy appearance, and the John Hancock Center at 875 North Michigan Avenue. On the 94th floor, there is an amazing observation deck called 360° Chicago, that tilts downwards by 30 degrees, at 1000 feet above street level! Some hotels in the area include Sofitel Chicago, The Drake A Hilton, and Raffaello Hotel.

Sports Venues

If you like sports, the Chicago Cubs’ famous Wrigley Field is worth a visit. It was purchased by the chewing gum magnate William Wrigley in 1921, and is the oldest National League ballpark. The Wrigleyville Hotel is located nearby, and is very modestly-price. On the South Side of Chicago, there is Guaranteed Rate Field, home of the Chicago White Sox. 

If you like football, Soldier Field, located near The Field Museum and The Shedd Aquarium, is the home stadium of the Chicago Bears, which dates back to 1924.

And for hockey and basketball, there is United Center, which is the home turf for the Chicago Blackhawks and Chicago Bulls.

Lincoln Park

In Chicago’s Mid-North District, there is Lincoln Park, with a number of attractions. There is the Chicago History Museum, with exhibits about the history of music in Chicago, film and art of Chicago, and notable Chicagoans, such as Martin Luther King Jr. and Abraham Lincoln (who was born in Springfield, but who used Chicago as his political headquarters).

The Lincoln Park Zoo has been operating since 1868, and has almost 1100 different animals under its care. Some notable sections of the 35-acre zoo are: the African Journey and Center for African Apes, the Pritzker Family Children’s Zoo, the Farm-in-the-Zoo, and McCormick Bird House.

The Lincoln Park Conservatory is a collection of thousands on species of plants, in a glass greenhouse dating from 1895. It consists of 4 separate houses: The Palm House, The Orchid House, The Fern Room, and the Show House. There is also the Alfred Caldwell Lily Pool--a serene pond surrounded by wildflowers.

The Peggy Notebaert Nature Museum is also in the same area. It features opportunities for kids to witness nature and science first-hand, learning about gardening, conservation, and the native species of insects, plants, amphibians, and more.

Getting around in Chicago

The Chicago Transit Authority (= CTA) serves Chicago and its suburbs, with an elevated train and bus system, as well as a commuter rail called Metra.

Elevated Train and Subway

The Chicago “L” (meaning “elevated”) train system is one of the oldest in the world, dating back from 1893. Like the New York subway system, it runs 24 hours a day--so even if you spend a night on the town, you have a way of getting home. There are 8 color-coded lines traversing Chicago, with a heavy concentration of lines running in the “Loop” area. The “L” presently costs $2.25 per ride, but you can get an all-day pass as well.

Bus service

The CTA runs a bus system as well, with 125 different bus routes taking you around the city and to the outlying suburbs. It’s best to consult an interactive map to know which bus line will get you to your destination.

O’Hare Airport vs. Midway Airport Transportation

There are two major airports in Chicago: O’Hare International Airport, and Midway International Airport. O’Hare receives traffic from all the major airlines. Midway Airport is more for domestic flights, only being served by Delta, North Country Sky, Porter, Southwest, and Volaris Airlines. But some say that the flight times are more reliable at Midway.

Water Taxi

Chicago has a passenger ferry service, known as a “water taxi” that travels along the Chicago River. It has stops at scenic areas in the city--and you have unlimited use of the taxi with just an $8 all-day pass.

Bike rental

The is the “Divvy bike” bike sharing service in Chicago, distributed around 580 stops in the city. You can rent a bike for a single ride for $3, or use a daily or even yearly rental plan There are some scenic bike paths in Chicago for which the Divvy is most suited, such as The 606--taking you through 2.7 miles of the Bloomingdale Trail, on the northwest side of Chicago.