Chicago Travel Guide

exploring the Windy City, chicago, in the midwestern united states
Chicago is the third largest city in the United States and is located on the southwestern shores of Lake Michigan. Best known as the “Windy City” because the politicians blow hot air, Chicago is one of my favorite cities. Its biggest draw today is its green space and architectural beauty, the most famous of which is Grant and Millennium park, home to the famous Chicago Bean. More than that, you’ll find world-class food, fun nightlife, lots of activities, and just a cool atmosphere. Visit in the summer when life on the lake comes alive. There’s not one person I know who doesn’t say “You can’t get better than Chicago in the summer.”

Typical Costs

Hostel prices – Hostels in Chicago average between $25-50 USD per night for a dorm room. A private room is around $80-100 USD for a double room.

Budget hotel prices – Budget hotels in Chicago start at around $80 USD per night and move up towards $150 USD (or more) when you get close to the city center.

Average cost of food – You can eat in numerous restaurants around the city for less than $20 USD. Chicago is home to many farmers markets for some fresh fruit and veggies, but the prices tend to be a bit higher than the supermarkets. You can cook your own food for $30-60 USD a week. For cheap eats, like burgers, hot dogs, and pizza, expect to pay around $6 USD for a meal.

Transportation costs – On the metro, a single ride is $2.25 USD per ride (If you’re a student, fare is as cheap as $0.75 USD). A transit card can be loaded with any amount from $2 USD, or as high as $100 USD. Transit cards are required to ride CTA trains, and are available from vending machines located at all train stations. There are also visitor passes that will allow you to have unlimited rides for a specific amount of days. 1-day: $10 USD, 3-day: $20 USD, 7-day: $28 USD.

Money Saving Tips

Purchase the City Pass – See major attractions in Chicago at about half the price with a City Pass which includes travelers’ picks for bars, restaurants, shopping, and neighborhoods.

Top Things to See and Do in Chicago

Be a kid at Navy Pier My favorite adventure in Chicago was to Navy Pier. Navy Pier is sort of like a carnival in a city. It contains some rides, a Ferris wheel, lots of restaurants, a Shakespeare theater, boat tours, an oddly large number of beer gardens, and even miniature golf.

Check out the Oriental Institute Museum – Despite its name, the collection has nothing to do with the Orient, but instead is a huge archaeological collection of objects from ancient Egypt. Still informative though.

Visit the Chicago Cultural Center – Former site of the Chicago Public Library, this lovely building is known for its exquisite Tiffany mosaics, especially in its performance venue, Preston Bradley Hall. It has changing art exhibits.

See Robie House – This Frank Lloyd Wright masterpiece, completed in 1909, is a premier example of his Prairie School design. Wright helped make Chicago architecture famous and this house is one of his best-known buildings.

Visit the Art Institute of Chicago – Visit the famous Art Institute of Chicago. From photography to architecture to textiles, this museum houses a permanent collection that includes works by Eva Hesse, David Hockney, and Ellsworth Kelly. On Thursday evenings (5-8pm) entry is free for residents of Illinois.

Relax in Grant and Millennium Park – Located right downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. You can also find people playing chess out here and during the summer they have a lot of free concerts. This is also where you will find the famous “Chicago Bean” sculpture.

Stop by the City History Museum – This museum provides a good overview of the history of the city, especially of the Great Chicago Fire that burned down most of the city.

See the Cubs play – Locals are fanatical about their baseball team. Get in the spirit and head out to a game. It gets really intense when the Cubs play Chicago’s other team the White Soxs.

Eat the famous pizza – Chicago developed the deep dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying at least one. The deep dish pizza was invented by Pizzeria Uno, which is now a national restaurant chain.

Stroll down the Magnificent Mile – This stretch along Michigan Avenue is known for its upscale designer boutiques. Even if you don’t want to blow your budget on some expensive threads, it’s still an experience to stroll down the avenue and take in the sights and the people.

View some war-inspired art – The National Vietnam Veterans Art Museum is a powerful yet seldom-visited museum. It features art that was created by Vietnam war veterans and, more recently, veterans from Iraq. It’s a stark reminder of the overly-romanticized notion of war.

Get acquainted with nature – The Peggy Notebaert Nature Museum is a beautiful institution with roof-top gardens, and plenty of information about the ecosystems surrounding Chicago. What is most interesting is the “butterfly haven” — an enclosed space with hundreds of butterflies, a waterfall, and garden paths.

Meet a local – Chicago has a local greeter program, which offers free walking tours of various neighborhoods from a knowledgeable local. This is a great opportunity to see more of the city from a more intimate, ground-level perspective.