Welcome to Chicago, a city of world-class restaurants and museums, theater, architecture, shopping, parks, a lake so big it can trick you into thinking you’re on the ocean, and more. From taking in history on a river tour to sipping innovative cocktails, biking along the lake or shopping your way down Michigan Ave, there truly is something for everyone.
Most importantly, Chicagoans love Chicago, and it’s always fun to visit a city where the residents are enthusiastic about showing it off. Need extra recommendations? Just ask. This is the Midwest after all.
Before you go, learn more about the history and culture of Chicago.
Couples who like city getaways; foodies seeking a mix of innovative global cuisine and seasonal Midwestern fare; families who love museums; just about anyone and everyone
Chicago has something for every budget, from inexpensive food stands to Michelin-star restaurants, hostels to high-end hotels. The average hotel price is around $150, but there are hostels closer to $25 and luxury hotels upwards of $400. Likewise, you could easily spend $100+ on a fancy dinner, but you can also grab a Chicago-style hot dog or some fantastic Mexican, Indian, Turkish, or Vietnamese food for around $10.
Like any major city, Chicago is mostly safe, but has some risks. Don’t leave your bag unattended on the metro or in a busy coffee shop, for example. Women should be careful walking late at night, like in most cities. Chicago has notoriously dangerous neighborhoods, mainly on the south and west sides. Gun violence in these neighborhoods is mostly targeted and highly unlikely to affect tourists.
Chicago is hot in the summer, frigid in the winter. Average temperatures from December to February are in the high 20s and low 30s, bumping up by about 10 degrees each month until July and August, where they hover in the 80s before crawling back down. It can be humid in the summer, and winds in the winter can often make it feel much colder than it actually is. It is typically cooler near Lake Michigan, on the east side of the city.
Chicago really comes alive in the summer, when residents take advantage of the weather and numerous outdoor activities, patios and parks. To avoid the hottest days, come in May, June, or early September but if you plan to hit the beach and don’t mind a little humidity, July and August can be fantastic as well. Fall (late September to early November) is also a beautiful time to visit.
December through March typically see the fewest crowds and lowest prices, but you’ll have to contend with some very cold days that can make sightseeing unpleasant.
See the city by foot or bike: Chicago is a fantastic walking city. Though it’s large, walking from neighborhood to neighborhood gives you a feel for the city and the little things that make each area unique. You can also walk or bike the entire north-south length of the city on the Lakefront Trail, which has exit points every few blocks to get back into the city.
Embrace free tourism sites: Some of Chicago’s most iconic attractions are also free. Millennium Park, home of Cloud Gate (better known as “the Bean”) is always free to visit and in summer months also has free concerts, movies and workout classes. A walk along the Chicago Riverwalk provides the city’s best views of beautiful, historic buildings like the Tribune Tower and Wrigley Building. You’ll also pass art installations, civic memorials and a floating garden. Around the city, keep an eye out for public art like Picasso’s “The Picasso,” Calder’s “The Flamingo,” Chagall’s “The Four Seasons,” and dozens of murals from local artists.
Visit museums for free or bundled rates. Chicago’s museums host free days multiple times a year. See if one of the dates times up with your trip. If not, and if you plan on visiting multiple museums and attractions during your stay, the CityPass offers a bundled rate.
In Chicago, chefs are celebrated and new restaurants open every week, meaning there’s a never-ending supply of fantastic food–but without the pretentious vibe that sometimes takes hold of great food cities. This is the Midwest after all. From hot dogs and tacos to Michelin-starred experiences, and everything in between, Chicago really has it all.
There are hundreds of hotels in Chicago, mostly concentrated in the Loop, River North and West Loop, though there are options in almost every neighborhood. Prices vary by season, but generally range from about $110 to $300. There are several popular hostels as well, with prices from about $25 to $100. Airbnb is a great option. There are homes listed in every neighborhood and in a wide range of styles and prices.
Lincoln Park: Lincoln Park is home to beautiful homes and lots of boutiques and restaurants, as well as the sprawling park.
Gold Coast: The swankiest neighborhood in Chicago, here you’ll find bars and restaurants where the point is to see and be seen. You’ll also find gorgeous historic mansions, especially on State St. and Dearborn St.
Wicker Park: An eclectic neighborhood with art galleries, vintage stores and cool fashion boutiques, bookstores and cafes, and lots of great food.
Lakeview: Lakeview encompasses a few smaller neighborhoods, like Wrigleyville, where you can catch a Cubs game, and Boystown, the city’s LGBTQ+ enclave.
Though geographically large, Chicago is easy to get around. Public transport is simple and affordable–the “L” train, or metro, is $2.50 per ride and the bus is $2.25. You can get pretty much anywhere in the city by bus or metro.
Uber and Lyft are another easy option. Taxis are less prevalent, but can be flagged downtown. Taxis and rideshare apps have similar prices. If you drive, pay attention to parking signs. In neighborhoods, parking is often free but there are restrictions on who can park where. Downtown, parking lot rates range from $20-$100 depending on the lot and time.
Chicago is home to two international airports—the huge O’Hare International Airport (ORD) and the smaller Chicago Midway International Airport (MDW). O’Hare is among the busiest airports in the country and sits about 14 miles from Chicago’s Loop. It’s a hub for both American Airlines and United Airlines, as well as a focus city for Frontier Airlines and Spirit Airlines. Midway Airport is about 12 miles from the Loop and a major base for Southwest Airlines.
The Chicago Transit Authority’s rail network (known as the L) connects to O’Hare via the Blue Line. Travel time from the airport to the Loop is about 45 minutes and a ticket costs $5. Taxi fares to downtown Chicago are generally in the $40 range and rideshare options (like Lyft and Uber) start at around $35-50 for the 25-90 minute (depending on traffic) drive.
The L also serves Midway Airport with the Orange Line. The trip from Midway to downtown takes about 25 minutes and a ticket costs $2.50. By car, the trip is 15-40 minutes (depending on traffic). Taxi fares start at around $25 and rideshare fares are about $25-40.
Starved Rock State Park: About 90 minutes from the city you can hike sandstone canyons and visit waterfalls at Starved Rock State Park.
Indiana Dunes National Park: Visit one of the nation’s newest national parks just 45 minutes from Chicago. Here you can hike sand dunes, swim in Lake Michigan, and spot rare bird species.
Oak Park: Ten miles west of downtown Chicago, the suburban village of Oak Park is home to the Frank Lloyd Wright-Prairie School of Architecture District, the largest concentration of Frank Lloyd Wright homes in the country, as well as the architect’s studio. The Ernest Hemingway Birthplace and Museum is also here, along with numerous restaurants and boutiques.
Milwaukee: Milwaukee is only 90 miles from Wisconsin, but there’s so much to do you’ll want to spend the night. Spend some time in the art museum, designed by Spanish architect Santiago Calatrava and drink your way through a few Wisconsin breweries. Don’t forget the cheese curds.
Galena: About 160 miles from Chicago, Galena was once a major port city and today is a tourist town that boasts hundreds of buildings on the National Register of Historic Places, including the home of Ulysses S. Grant. The historic downtown is cute and full of shops and restaurants. In the winter, you’ll find some of Illinois’ only ski slopes in Galena.
Ferris Bueller’s Day Off: There are many movies filmed in Chicago, but this one is like a love letter to the city. Watch for scenes at Wrigley Field, the Art Institute of Chicago and plenty of great skyline shots.
Hoop Dreams: This documentary follows two students recruited from the South Side of Chicago for a prestigious basketball program, and looks at issues of race, class, and education.
The Devil In the White City: This book, based on a true story, tells the behind the scenes story of the 1893 World's Columbian Exposition from the view of designer Daniel Burnham, while also telling the story of serial killer H.H. Holmes.
Dreams From My Father: Barack Obama’s first book was published back in 1995, before he was a politician. It tells the story of his life, including many scenes in Chicago, where he worked as a community organizer at the time and met Michelle Obama.
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