Almost every article about Chicago begins with one of three facts: Chicago is the city of gangsters who ruled here in the 1930s; Chicago is the windy city; Chicago is the third largest city in the United States.
Of course, all of these are true. But these three facts won't reveal how soulful Chicago is and how much you'll love it at first (well, maybe sometimes second) glance.
Chicago is drawbridges, friendly people, and uniqueness. It's skyscrapers, parks, a huge lake, and hidden bars. If this city finds its way into your heart, believe me, it will stay there forever.
Chicago's Transportation System
The transportation system in Chicago is called CTA - Chicago Transit Authority. On their official website, you can download the schedule for the desired bus, plan a route from point A to point B, or reload your fare card. The subway fare is $2.50 (you'll have to pay $5 from the airport to downtown), and the bus fare is $2.25. Within a two-hour period, you can make two transfers, which will cost only 25 cents each. There are daily passes ($10), 3-day passes ($20), and weekly passes ($28) available for purchase at every subway station and at the airport.
Chicago is a wonderful city to explore on foot as most of the attractions are within walking distance. However, if you want to reach more distant neighborhoods, such as the residential area from the movie "Home Alone," you can easily use public transportation.
If you stay out late or find yourself in a bar, you can always rely on transportation to get back to your hotel as it operates 24/7.
An excellent way to experience Chicago is by bicycle. You can rent one along the waterfront and ride along the entire lake. For example, here.
Charter a bus from New York to Chicago at an inexpensive price is possible in the bus company Comfort Express Inc.
Accommodation in Chicago
Chicago is one of the expensive cities in America when it comes to housing, especially during the high season. Be prepared to pay around $100 per night in a hotel (unless you come across discounts). We recommend staying in neighborhoods along the lake, from Near North Side to Chinatown, as they are closest to the main attractions. Here is a selection of pleasant hotels that are easy on the eyes and the wallet.
Chicago Parthenon Hostel (310 South Halsted Street) is conveniently located in the heart of Chicago. You can reach Willis Tower within a 15-minute walk. A private room with a shared bathroom on the floor will cost around $80, while a bed in a dormitory room is priced at $40. For this price, you'll get a good location, breakfast, and Wi-Fi. However, some guests have complained about the Wi-Fi, so you may need to head to one of the many cafes in the area for internet access. HI Chicago Hostel (24 Ida B Wells Drive) is part of a hostel network that stretches from the West Coast to the East Coast of the USA. For $40 per bed, you'll enjoy a free breakfast, a prime city center location (just a 5-minute walk to Millennium Park), and a spacious common area with billiards and table tennis. One downside is that the hostel is located near the subway tracks, so don't forget to bring earplugs to drown out the noise.
The Palmer House Hilton (17 East Monroe Street) is situated right in the heart of The Loop district and captivates visitors with its lobby, where the ceiling, walls, and furniture make you feel like you're in a museum. The hotel often has sales, allowing you to snag a double room for around $100. As a bonus, you'll have access to a free swimming pool and fitness center.
At the Wyndham Grand Chicago Riverfront (71 East Wacker Drive), you have a chance to get a room on the top floor with a breathtaking view for a relatively reasonable price (if you're lucky). During discounts, a room for two can cost around $110. The hotel is located across from the Trump Tower and the Wrigley Building. Try negotiating with the manager and request a room with a good view. The United States is known for its excellent service, so they might be accommodating.
Don't forget that Airbnb, Couchsurfing, and Craigslist are well-developed in America. If you haven't tried finding accommodation with locals on these websites yet, now is the perfect time to start!
Cultural Program
In Chicago, like in any other city, there are must-visit places. Among them is the famous sculpture Cloud Gate (sometimes referred to as "the Chicago Bean") and the Lake Michigan waterfront. However, Chicago has much more to offer than just these iconic locations.
Chicago is a "multi-level city" consisting of three levels: an underground level for cars (an attempt to reduce traffic congestion), the main visible level, and the elevated level for the subway.
Most of the Chicago subway stations are located above ground, so if you're unlucky with the weather, hop on the Pink or Green Line and take a ride through the city center.
If the weather is sunny and warm, start your exploration of the city with a walk in The Loop district, recognized as one of the most beautiful areas in Chicago. Here you'll encounter wide boulevards, office workers, and skyscrapers. Chicago's architecture is unique, and despite the initial impression of being another New York, you'll notice significant architectural differences over time. Key attractions in this district include Calder's Flamingo sculpture, the famous Chicago Theatre marquee, and the Willis Tower skyscraper (233 S Wacker Dr). If you're a fan of road trips, don't miss the start of the famous Route 66, which extends from this area all the way to California. The sign can be found here: V9HG+R5 Chicago, Illinois, USA.
Chicago has a deep-rooted love for skyscrapers. For instance, there's the skyscraper prison (71 W Van Buren St), Marina City (315 N Dearborn St) - "the corn cob," which houses cinemas, restaurants, and apartments, and the Chicago Temple Building (77 W. Washington St), which doubles as a church.
The title for the best observation deck is contested between the Sky Deck in the Willis Tower and 360 Chicago in the John Hancock Center. The Sky Deck is a famous observation platform with a transparent balcony on the 103rd floor. It's worth noting that the glass floor has cracked a few times while tourists were standing on it, most recently in June 2019. No one was injured because the balcony consists of multiple layers of glass, ensuring safety. The entrance fee is $27, and you can purchase tickets online.
360 Chicago, located on the 94th floor, is slightly lower. It costs $25 for admission. By paying an additional $3.5, you can get a ticket that's valid for 48 hours, allowing you to enjoy both daytime and nighttime views of the city. To learn how to enjoy the city panorama for just $10, check out the "Bars" section.
Make sure to take an architectural cruise along the Chicago River. During the cruise, you'll receive a guided tour (in English) about Chicago's unique architecture, making it one of the most beautiful ways to experience the city. The cruise lasts for an hour, and tickets can be purchased online for $45. Even on a warm day, bring warm clothes as it can be quite breezy on the water. If you're visiting during the colder months, be prepared to keep your hands, nose, and the rest of your body warm. To save money, look for discount coupons, as they frequently appear on Groupon.
Chicago is closely connected to Lake Michigan. Along the lake, there's a 30-kilometer-long Lakefront Trail (from Ardmore Street to 71st Street) that's perfect for walking, cycling, running, or rollerblading. Choose your preferred activity and enjoy! If you want to take a break, stop by one of the city beaches and go for a swim (if you're not afraid of the cold). Good beaches to visit include 57th Street Beach, Foster Beach, and 31st Street Beach. They are less crowded and relatively clean.
Don't miss a stroll along the Chicago Riverwalk. If you're an early bird and find yourself there at 9 am, you'll witness the opening of the drawbridges, which, as it turns out, are not exclusive to St. Petersburg. Check the schedule here.
For architecture enthusiasts, Tribune Tower (435 N Michigan Ave), The Wrigley Building (400-410 N Michigan Ave), and Assumption Catholic Church (323 W Illinois St) in the River North district are not to be missed.
If you're into modern graffiti, head to Milwaukee St. This street is a typical American one-story neighborhood by day and a vibrant area at night. Here are the coordinates of a few graffiti locations worth admiring during daylight hours: W8C4+F3, W895+GW, W878+PP, W83M+5G. Details on what to do in the evening can be found in the "Bars" section.
If you want to escape the tourist crowds, venture into the Pilsen district, specifically W 18th St. Along this street (from S Racine Ave heading west), you'll find beautiful vintage houses, many of which are adorned with modern street art. Additionally, the area boasts numerous excellent Mexican cafes and restaurants. Take your pick and indulge.
In the evening, visit the Navy Pier. Once a genuine military training base, it has now become a popular destination among residents and tourists, hosting fairs and festivals. You'll find numerous cafes and souvenir shops here (feel free to browse, but be aware that prices are often inflated). One of the most popular attractions at the pier is the Ferris wheel (tickets cost $16). By the way, it was one of the first Ferris wheels in the world, built in 1893 (don't worry, the mechanisms have been regularly updated since then). The pier is a fantastic place to spend an evening, leisurely strolling through The Crystal Gardens (pathways amidst rare plants), reaching the end of the pier where you'll find tables to enjoy a windy sunset.
Parks
A must-visit stop should be Millennium Park and its extension, Grant Park. This is a iconic place for locals, as it is home to the famous Cloud Gate sculpture. Make sure to be there at sunset when the sunlight beautifully reflects off the skyscrapers. The park also hosts festivals and outdoor concerts. Bring a blanket, sit on the grass, and enjoy the music along with the scenic views and local food. Notable attractions in the park include Buckingham Fountain, Lurie Garden, and Crown Fountain.
Lincoln Park is home to a small zoo, which can be visited for free, as well as a crescent-shaped waterfront (coordinates: W97H+VV), offering the best view of the downtown area.
Maggie Daley Park is located across the road from Millennium Park. It features numerous playgrounds (who said only children can enjoy swings?) and the picturesque BP Pedestrian Bridge, which connects both parks.
At Garfield Park, you can sit by the pond, have a picnic, and admire the Garfield Park Gold Dome Field House. Originally built as an administration building for the park, it now houses a high school, a dance school, and a fitness center. In the northern part of the park, there is a donation-based conservatory. Here, lectures and exhibitions are frequently held. Stay updated on their events through the official website.
Humboldt Park also offers ponds, playgrounds, and tennis courts. Additionally, it houses the Puerto Rican Cultural Center in Chicago, featuring a café with local cuisine and a museum of Puerto Rican art. The park hosts the Puerto Rican Festival and the Latin Jazz Festival.
The 606 trail (from 1600 West Ashland to 3732 West Ridgeway) is an equivalent to New York's High Line park. Both are built on abandoned railway tracks. The park is perfect for walking and engaging in sports activities. Occasionally, festivals and musical evenings take place here.
Museums
The aforementioned National Museum of Puerto Rican Arts & Culture (3015 W Division St) will appeal to those interested in Puerto Rican culture. Even if you're not interested, appreciate the museum building itself, which bears little resemblance to the American style. The museum is closed on Sundays and Mondays, and admission is free (any donation of your choice is welcomed).
Another museum dedicated to a different culture is the National Museum of Mexican Art (1852 W 19th St). Here, you can learn about the history and art of Mexicans. The exhibitions are always changing, but one thing remains constant: admission is always free, though donations are still welcomed. The museum is closed on Mondays.
The classic museums, Art Institute of Chicago (111 S Michigan Ave) and the Museum of Contemporary Art (220 E Chicago Ave), are relatively close to each other. Decide what interests you more: classical or contemporary art. A ticket to the Art Institute of Chicago will cost you $27 (it will be cheaper with a City Pass combination), while the Museum of Contemporary Art has no fixed price, only a recommended donation of $15 (but you won't be judged if you pay less). By the way, if you decide to visit the Art Institute of Chicago, don't bring a backpack with you as they only allow small bags inside. You'll have to pay $1 (cash only) for storage and then wait in line to retrieve your belongings.
If by chance you do visit during winter (though we warned you), half of the cultural program will be inaccessible due to the extreme cold and wind. Here's a selection of places to visit during this time of year (especially relevant if you're visiting in December for Christmas):
Millennium Park has a free ice skating rink
Daley Plaza hosts a traditional market with stalls where you can buy souvenirs, toys, or warm up with mulled wine.
At the Museum of Science and Industry (5700 S Lake Shore Drive), the annual Christmas Around the World festival takes place, featuring over 50 Christmas trees that symbolize holiday cultures from around the world. Among the displays, you can find trees from Russia, Belarus, and Ukraine.
Lincoln Park Zoo also sets up illuminations when the animals go into hibernation. You can also see ice sculptures here.
A holiday tram called the HOLIDAY LIGHTS TOUR operates in the city center. The tours start from 360 Chicago. The cost is $32.
Snacks and Fast Food
There are two things you must try in Chicago: Chicago-style pizza and Chicago-style hot dogs.
Chicago-style pizza is a small pie with deep-dish crust filled with cheese and your choice of other ingredients. The cheese is placed under the toppings, unlike in traditional pizza, to prevent it from burning. For the best deep-dish pizza, head to Pequod's Pizza (2207 N Clybourn Ave), Lou Malnati's Pizzeria (439 N Wells St), or Giordano's (700 E Grand Ave). The iconic spots are Pizzeria Uno (29 E Ohio St) and Pizzeria Due (619 N Wabash Ave), where it is believed that this style of pizza was invented in 1943. A small pizza, which will surely keep you full for hours, costs around $10 on average.
A Chicago-style hot dog consists of a beef sausage topped with onions, spicy peppers, relish, tomatoes, and mustard. No ketchup allowed! You can try and savor this delicious hot dog at HotGDog (5009 N Clark St), Devil Dawgs (767 S State St), or Downtown Dogs (804 N Rush St).
If you're craving an authentic American burger, forget about McDonald's, Burger King, and KFC. Instead, try the Butcher & The Burger (1021 W Armitage Ave) where you can get the classic All American Burger for $9.95. If you're feeling adventurous, they offer burgers with salmon, shrimp, or bison.
Make a stop at Burger Bar Chicago (1150 S Michigan Ave). Along with a wide selection of burgers and appetizers, try the famous Canadian dish that sounds oddly familiar to every Ukrainian person - poutine. It's fries topped with cheese and gravy. The place also offers a great selection of local beers.
If you're a fan of the movie "Ted" or actor Mark Wahlberg, visit his establishment, Wahlburgers (2 E Ontario St). We recommend trying The Impossible Burger with their signature dressing for $13, which is made from plant-based meat.
Don't forget to try the mac'n'cheese at Kuma's Corner (852 W Fulton Market). For $14.5, you can add two additional ingredients to the classic recipe.
If you're planning a picnic in Millennium Park, stop by Epic Burger (517 S State St). For $7, grab a burger (they have vegan options too), a milkshake, and head to the lawn.
Delicious classic pizza is served at The Boiler Room (1307, 2210 N California Ave). The menu offers over 30 varieties of pizza, both classic and in the Chicago-style. Please note that this cafe only accepts cash.
Shopping
Magnificent Mile. The name of this district in Chicago is synonymous with "shopping." Magnificent Mile is lined with stores along Michigan Ave. Here you'll find both luxury brands and mass-market retailers like Zara, Nike, Banana Republic, and more.
Macy's (835 N Michigan Ave, 111 N State St). A well-known mall in the USA, found in almost every major American city. Inside, all the stores are situated in one place rather than separated. Here you can find discounted clothing from brands such as Levi's, Ralph Lauren, Michael Kors.
Another street with shops is State St (from Lake subway station to Jackson). Visit this street if you need cosmetics (Sephora, Lush, Urban Decay), footwear (Forever 21, Footaction, Crocs), or simply enjoy strolling through the shopping center (T.J.Maxx, Nordstrom).
Marshalls (1101 S Canal St, 600 N Michigan Ave, and other locations) or Ross Dress for Less (26 E Randolph St) are well-known chain stores where you can find great clothing at affordable prices (especially during sales in January and July).
Clark Street Sports (1960 W Madison St). Surely, you had a t-shirt/cap/jersey with the famous red bull logo of the Chicago Bulls team during your childhood. At this store located near their home stadium, you can purchase any souvenir or clothing item featuring the logo of this renowned team.
If you want to feel like a gangster, visit Jack Schwartz Importer (141 W Jackson Blvd) for cigars. This store has been open since 1921, and it was where famous gangsters used to buy cigars. Today, they offer a wide range of cigars, some of which are exclusive to this store (such as their signature "Westminster" cigars).
If you happen to get tired of the clothes you brought, head to stores that operate on a buy-sell-trade principle: Buffalo Exchange (1478 N Milwaukee Ave) and Crossroads (2711 N Clark St). In these places, you can sell your clothes (for future buyers or recycling) and choose something suitable for yourself on the spot. Sometimes, you can find very unique items in these stores. Note that the clothing must be in perfect condition.
For clothing from local designers, visit Squasht Boutique (2556 W Chicago Ave). They sell women's clothing and accessories.
If you're a Marvel or DC fan, drop by for comics (even if you don't speak English well). Stock up at First Aid Comics (1142 W Taylor St). Comic prices start from $4.
If you enjoy bringing souvenirs from your trip, check out Transit Tees (1371 N Milwaukee Ave) or Urban General Store (4723 N Lincoln Ave). Prices here will be significantly lower than in the touristy areas of Chicago. If you don't want to travel that far, stop by a Walgreens pharmacy or Target department store.
Visit Pinwheel (1722 W 18th St) if you want to buy CDs or vinyl records. Even if you have nowhere to listen to them, drop by for the atmosphere. After all, Chicago is one of the capitals of blues.
