A beginner’s guide to Chicago
People tend to fall in love with Chicago very quickly – and it’s not hard to understand why.
The city has plenty to do: including sports, shopping, fun fairs, museums and even a beach! But there’s a vibe about Chicago that you can’t mistake. It’s buzzing, but it’s also friendlier than your average large metropolitan. We recommend that every city-lover stops by Chicago at one point in their life – and here’s our guide to making the most of any visit.
What to see and do
Chicago’s vast size can be daunting for first-time visitors with so many attractions to pick from. While we’d encourage you to research everything Chicago has to offer and decide what’s right for you, we’ve pulled together a selection of Chicago’s best sights.
One of the most relaxing ways to take in the beautiful sights of Chicago is on a boat tour along its river and lake. Choose between Chicago’s First Lady and Shoreline Sightseeing, or get adventurous with Kayak Chicago.
Stroll through Millennium Park
You’ve probably seen the pictures of a bean-like structure in Chicago? You’ll find it here in Millennium Park. Amongst the 25-acres of public space, you’ll find FREE art installations, outdoor concerts, film screenings, outdoor workouts, and tours. In winter there’s also an outdoor ice-rink.
Shop along Magnificent Mile
Chicago is home to a very eclectic and stylish shopping scene, with the Magnificent Mile as its epicentre. This cosmopolitan, history-packed strip on downtown Michigan Avenue (between the Michigan Avenue Bridge and Oak Street) is home to department stores, multi-story megamalls, luxury boutiques and brand name retail chains.
Visit larger-than-life galleries
The world-renowned Art Institute of Chicago hosts one of the biggest collections of late-19th-century French art in the world. While the Museum of Science & Industry is the largest science museum in the Western Hemisphere. Oh, and The Field Museum is home to Titanosaur, the largest dinosaur to roam the Earth.
You could spend a week just exploring the museums and art galleries. There’s museums that document and celebrate African-American heritage, Jewish tradition, Mexican art, Lithuanian culture, Ukrainian history, Puerto Rican culture, military history, maritime history, and even an American Writer's Museum.
Catch a sports game
Chicago loves its sports, particularly soccer, baseball, football, basketball, and hockey. There’s always a game happening in Chicago so it’s worth searching for one while you’re in town.
Chicago is famous for its deep-dish pizza, and while there is more to the city’s food scene than this – you will still find a lot of pizzerias. Lou Malnati in the River North area is generally regarded as the best place to stop by for a slice of this famous dish.
Other foods that are quintessentially Chicago include their own style of hot dog (it’s topped with vegetables), Italian beef (a style rarely found outside the city), and steak (Chicago is the meat-packing capital of the world). For something a little different, you can visit the old haunts of Al Capone, such as the Green Mill Cocktail Lounge or the Green Door Tavern.
Chicago was once awarded "City of the Year" by GayCities.com, and its gay district Boystown was named “best gay neighbourhood in the world" by Out Traveler magazine. It’s no wonder though as Chicago boasts a rich and proud LGBTQ history, which you can learn all about with an LGBTQ+ Landmarks Tour, or by strolling the Legacy Walk in Boystown. There’s also a selection of LGBTQ+ businesses, ranging from bookstores to nightclubs.
Getting to Chicago and finding your way around
Chicago is the home of United Airlines, so there’s no shortage of flights. There are several flights to Chicago a week from the UK, including a new service from Edinburgh to O’Hare International Airport. O’Hare International Airport is home to an on-site hotel, a yoga room, mother’s room, and an aeroponic garden.
Once you’re in Chicago, The El (short for the CTA's elevated train, which also includes subway trains) offers a quick and inexpensive public transportation option. If you need to get out to the suburbs, Metra Trains from Union, Ogilvie, and La Salle Street stations provide several convenient routes.
If you’re not going very far and just want to explore the city centre, it’s easy enough to hail a cab. Lyft and Uber also have a presence within the city.
If you’re a keen cyclist, you can also make use of the city’s bike-share service, Divvy. Their bike rental stations can be found across the city, where you can pick up one of their unmistakable blue bicycles. If you’re walking, Chicago’s streets are laid out in a handy grid system.
Other important information:
- Chicago is at its best during the summer months (though we recommend wearing layers)
- You’ll need a US Visa and US Dollars
- Tipping is customary in Chicago