If you love music, food, architecture, and art, Chicago is your kind of city.
Art lovers can spend days wandering around the Art Institute of Chicago, music lovers can spend every evening listening to blues and jazz acts at historic venues like the Green Mill, while architecture fans can join guided tours of Downtown Chicago and see every Art Deco building the city has to offer.
The Windy City is also a hub for shoppers – with the craft market at Lincoln Square, the endless supply of boutiques on Michigan Avenue, and city center malls like Water Tower Place.
Everyone can find something that their taste buds will savor, whether it’s the deep dish pizza at Lou Malnati’s, the burgers at DMK, the Polish food at Red Apple Buffet, or the Mexican food at Taco Joint.
You’ll never be bored when you visit the Mid West’s capital, so start planning your trip today.
Chicago’s Downtown district is packed with incredible twentieth century architecture. There are works by famous architects like Louis Sullivan (the Wainwright Building or the Auditorium) and Frank Lloyd Wright (the Rookery), as well as towering skyscrapers like the Sears Building and the Hancock Tower.
Chicago is a sporting city. Watch the Cubs play baseball at Wrigley Field, see the Bulls compete in the NBA at the United Center, or catch a Bears NFL game at Soldier Field.
Chicagoans love to eat. Try specialties like the deep dish pizza at Lou Malnati’s (439 N Wells St), Polish hot dogs from Maxwell Street (601 S Sacramento Blvd) or irresistible barbecue ribs from Blackwood BBQ (305 W Lake St).
Chicago has a vast collection of galleries and museums to explore. The Field Museum (1400 S Lake Shore Dr) has an enormous natural history collection, the Art Institute (111 S Michigan Ave) houses great works of art by masters like Seurat and Hopper, while the Museum of Science and Industry (5700 S Lake Shore Dr) will keep everyone entertained with exhibits like a restored German U-Boat and a reconstructed coal mine.
Chicago is also a city of art and music. In the early 20th century, it gave birth to a distinctive Blues sound, and you can hear the heirs of major artists like Buddy Guy and BB King at venues like the House of Blues (329 N Dearborn St). Jazz is another speciality, and fans should catch a show at the Green Mill (4802 N Broadway St) which was once owned by an associate of the infamous American gangster, Al Capone.
The Chicago Bears may only have the one Superbowl victory, but the atmosphere at Soldier Field is incredible. If you visit during the season, be sure to book tickets.
The Adler Planetarium (Museum Campus, 1300 S Lake Shore Dr) is a beautiful building on the outside, but it's the shows inside that are breath-taking. Watch high definition footage of space exploration, galaxies, and the solar system in a fully-immersive environment, a must for science fans.
When you visit Chicago, why not eat like the natives? Chicago has given birth to some mouth-watering dishes. Try the Italian deep dish pizza at places like Lou Malnati’s or Vito & Nicks, the Polish sausages at Jim’s Original, or the chicken Vesuvio at Sabatino’s.
Walk past endless boutique stores and window shop for the latest fashion items on 'the Magnificent Mile', and stop off at local cafes and restaurants like the Purple Pig (no. 500) or Spiaggia (no.980), one of Chicago’s finest Italian eateries.
Some of the best views of Chicago’s skyline are only visible from way out on Lake Michigan, so if you want the best possible vacation photos, a boat tour is a must. Head out with companies like Shoreline Sightseeing for architecture tours along the Chicago River, trips onto the lake, or the chance to watch the summer fireworks display at Navy Pier (Wednesday and Saturday evenings, May through to September).
If you are thinking about visiting Chicago, the climate is definitely a factor in deciding when to go. Between late November and March, the city can be bitterly cold, making late spring, summer, or early fall the best times to visit. A visit in September or October makes sense. The weather is pleasant and the city hosts some of its most exciting events, such as the Chicago Jazz Festival (September 1-4) and the International Film Festival (October 13-27).
The majority of visitors to Chicago touch down at O’Hare International Airport, which is about 20 miles north of the city. From there, the best route into town is to take the CTA Blue Line, which runs 24 hours a day, takes just over 30 minutes to reach the Loop and costs $5. If you land at Midway Airport in the south, the best route into town is via the CTA Orange Line, which takes about 25 minutes. Taxis are an option from both airports and will cost over $40 (excluding tips) from O’Hare and $30 from Midway. Car rental services like Budget and Enterprise, are also represented at both airports.
Chicago grew up as a rail terminus, and it’s still easy to travel there using Amtrak services. The main station is Union Station (which is a sight to behold in itself, with its vaulted glass ceiling). Services include the Homewood (to New Orleans), the Joliet (to Los Angeles), the Summit (to St Louis) and the Cardinal (to New York City).
From the east, drivers tend to take I-90/94 which links Chicago to New York and Philadelphia. I-65 runs south to Kentucky and Tennessee, while I-55 and I-57 connect the city to south-western destinations like St Louis and Kansas City. All interstates feed into the center of town, so it should be easy to reach Downtown accommodation by car.
Bus companies running services to Chicago include:
Megabus – Connects Chicago to a huge range of destinations, including Detroit, New York, Indianapolis and Dallas.
Greyhound – Runs buses to their stop at 630 W Harrison St. Destinations include New York, Los Angeles, Las Vegas and Philadelphia.
Burlington Trailways – Runs buses to destinations in the Midwest, including Des Moines and Omaha.
Indian Trails – Runs buses to destinations in Michigan.
If you are looking for a solid Downtown hotel, the Autograph (333 N Dearborn St) or the Peninsula (108 E Superior St) are good options. On the North Side, the Kinzie Hotel (20 W Kinzie St) is comfortable and convenient, while Hotel Indigo (1244 N Dearborn Pkwy) is a good, budget choice. On the South Side, you can’t do much better than the Amber Inn (3901 S Michigan Ave), while suburban options in the south include the Chicago Lake Shore Hotel (4900 S Lake Shore Dr).
Downtown – Downtown Chicago is a cultural, shopping, and entertainment center. Many people could spend their entire vacation Downtown without needing to head to the outer districts. Here you’ll find great museums like the Art Institute of Chicago alongside some stunning architecture. There are Art Deco masterpieces, like the Carbide and Carbon Building, and modernist towers like the Federal Center and the Rookery, with its astonishingly beautiful interior staircases. Downtown is also home to cultural attractions like the Auditorium Theater and Chicago Symphony Orchestra, so it’s the place to stay if you love opera, theater, or classical music.
The North Side – A prosperous part of Chicago that suits visiting families, the North Side has plenty of appeal. You can watch the Cubs play at Wrigley Field, catch rock bands at Metro or head to the retail market at Lincoln Square to check out the records, books and antiques. There are also plenty of ways to relax, including a night of bowling at Timber Lanes or the cutting edge comedy available at iO Theater.
Hyde Park – Located on the South Side of Chicago, Hyde Park is a predominantly African-American district with a glorious history. Once the home of Muhammad Ali and the writer Saul Bellow, Hyde Park was where U.S. President Barack Obama worked as a community organizer and it’s also home to the prestigious University of Chicago. Attractions include the Drexel Fountain and the Isidore Heller House designed by Frank Lloyd Wright, but the major appeal of the area is its culture. Sample great fried chicken at Harold's Chicken Shack (1208 E 53rd St) and follow that up with a night of blues at the New Checkerboard Lounge (5201 S Harper Ct).
Chicago’s public transit system is efficient and cheap, and is the best way to get around the city. The primary transportation methods are the trains and buses operated by the Chicago Transit Authority (CTA). To ride CTA vehicles, you’ll need to purchase a Ventra card ($5) from stations or kiosks. When you have a card, each train journey on the network costs $2.25 (with an extra $0.25 every time you change lines) while bus journeys cost $2. Travelers can also purchase a weekly CTA pass ($28) or a monthly pass ($100). Be aware that Metra commuter trains do not accept Ventra cards, so travelers will need to purchase tickets separately before they board.
Standard taxi fares are $2.25 as a basic charge, then $0.20 for each ninth of a mile after that, with an extra $1 fuel surcharge for every journey and another $1 surcharge for each extra passenger. Uber charges a basic rate of $1.70 and then $0.20 per minute or $0.90 per mile (along with a $1 safe ride fee and a $0.30 transit tax).
Locals generally advise visitors not to drive around the center of Chicago if they can avoid it, and with such a good public transportation system, it’s not usually necessary. Parking is expensive, at $35 per day, and traffic within 'the Loop' is almost always heavy, making catching the subway the quicker option. Navigation can be tricky as well thanks to inner city streets with multiple levels, while Chicago’s drivers are famously aggressive. If you have the nerve and are a quick learner, driving is possible, but most people will prefer sticking to public transit and taxis.
Chicago is cheaper than New York and San Francisco, but is slightly above average for American cities. Expect to pay $15-30 for a medium-range meal, $2.90 for 12 eggs and around $50 for a good pair of jeans.
Chicago’s major shopping street is Michigan Avenue (also known as the 'magnificent mile'), where you’ll find a wide array of boutiques like Chanel, J Crew, and Ermenegildo Zegna. For records, crafts and books, check out Lincoln Square. Book Cellar is ideal for readers, ornaments and antiques can be found at Eclecticity, and health and beauty products are available at Merz Apothecary.
Chicago has a broad range of supermarkets, with major names like Aldi, K-Mart, Walmart, Trader Joe’s Whole Foods, and Jewel-Osco all represented, so finding groceries will rarely be an issue. It’s also the home of Walgreen’s, so drug stores are everywhere.
Food is one of Chicago’s great passions. Italian food is one of the city’s specialties, and fantastic deep dish pizza can be found at Vito & Nicks (8433 S Pulaski Rd), while the Pasta Bowl (2434 N Clark St) is the place to go for a more expansive menu. Alinea (1723 N Halsted St) is a great, up-market American eatery while The Gage (24 S Michigan Ave) blends craft ale, great pub food, and views across Millennium Park. Superb Chinese food is available at Great Seas (3254 W Lawrence Ave), and Lao Sze Chuan (2172 S Archer Ave). For an authentic Polish hot dog, the best place to go is Jim’s Original (1250 S Union Ave), and unpretentious but delicious Italian beef sandwiches can be found at Joe Boston’s (2932 W Chicago Ave).
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