Chicago, Illinois

Chicago is the second-largest city in the Midwest and the third-largest in the United States. There are 77 distinct cultural areas within Chicago, each with their own personality and vibe. This means that there is something for everyone regardless of where they live. You'll find the right scene for your mood. It could be the artsy vibes of Wicker Park/Bucktown or the historic charm of the 19th-century Pullman Historic District.

Chicago has a lot to offer. The Chicago Riverwalk runs 1.25 miles between Lake Michigan and Lake Street. There are many places to stop for refreshments, such as bars and wineries, cafes and bars, as well public art installations, museums and monuments.

Chicago is home to a vibrant theater scene. It's known as the birthplace for improv comedy through groups such as The Second City. The Steppenwolf Theatre Company is one example. It has had an all-star cast that includes Gary Sinise and John Malkovich over the years.

Chicago Shakespeare Theater hosts 20 productions each year and 650 shows every year. These include musicals, plays, musical premieres, family programming, and all are inspired by (arguably), the greatest playwright in the world.

It is also one reason Chicago is one the most popular cities in America. Chicago's famous deep dish pizza is a classic Chicago style. It was invented in the 1940s and is instantly recognized for its bowl-shaped crust with cheese, sauce, toppings, and toppings. Chicago is more than deep dish pizza. Chicago is a city that you could eat your way around for months!

Best Time to Visit

Many consider the shoulder seasons of Spring (April-June), and Fall (September–October) to be the best times to visit the city. These are when the temperatures are mild, and there are many festivals and events.

Summer can be very hot and busy. Chicago winters are notoriously cold, but you can find more affordable accommodations and use the winter season to explore Chicago's indoor attractions like its famous museums and vibrant theater scene.

Pro Tip

There is a great mass transportation system, and ride-sharing. Downtown parking is quite feasible.

Airport

With our flight discounts, you get down at Chicago O'Hare International Airport (18 miles away) and Midway International Airport (12 miles) are the best options for flying into Chicago. Both airports cater to domestic and international flights and are easily accessible to downtown.

Best Things to Do

Enjoy Kayaking on the Chicago River
Located in the Avondale area, the Chicago River’s North Branch offers a bit more of a nature-infused Chicago kayaking experience than the areas located closer to downtown. Instead of big skyscrapers and busy streets, you’ll find green riverbanks and quieter stretches of water here. Townhomes and quaint cottages replace high rises and offices. All in all, this is a much more tranquil area to go kayaking in Chicago, away from the stress and bustle of downtown.

Explore the Morton Arboretum
The Arboretum conducts ongoing leading scientific research on tree health and tree improvement, collects and displays trees for study and enjoyment on the grounds, offers educational programming for adults and children and presents nature-related activities year-round for people of all ages and interests. The living collections continue to inspire visitors to appreciate, learn about, plant, and protect trees.

Visit Ping Tom Memorial Park
Just blocks away from Chinatown Square—Ping Tom Park has a special serenity to it. With its pagoda-style pavilion and bamboo gardens, the park is inviting to relaxing strolls, leisurely biking and roller-skating, and small gatherings along the river. Afterward, you’re close to some of the best dim sum and boba tea Chicago has to offer.

Take a Walk at Midway Plaisance
Located in the Hyde Park community, Midway Plaisance is a special-use facility with an ice skating rink which totals 83 acres and it features a warming center. Green features of the park include a north and south winter garden. Outside, the park offers the ice rink and multi-purpose fields. Many spaces are available for rental including our ice rink, warming center, and fields.

Meet Rare Wildlife at Lincoln Park Zoo
In a city where skyscrapers are built every day, Lincoln Park Zoo is dedicated to being the place in Chicago for all things wild—where children learn to love animals, where adults rediscover what it’s like to wonder, and where nature isn’t just an escape, but a priority. Thinking of picnic? This is the spot!

Recommended Hotels

You can find great options in the vicinity of the Michigan Mile, including amazing shops and restaurants. The Omni Chicago Hotel offers suite-style accommodation for a more luxurious experience. Fairfield Inn And Suites offers something more affordable.

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