Chicago Travel Guide - Best of Chicago

Chicago is ranked as the third-largest metropolitan area in the United States and the most populous city in the Midwestern. This city by the lake, also known as the windy city, is situated in the Great Lakes region of northeastern Illinois. Beyond the City of Chicago, the greater Chicagoland area extends into the neighboring states of Wisconsin and Indiana. The windy city is also culturally diverse with approximately 2.7 million residents. There are 50 districts or 77 designated community areas in the City of Chicago, the Loop is the central business district and home to the tallest skyscrapers, top attractions, and shopping areas.

Situated near the southern tip of Lake Michigan, Chicago started as a small trading post at the mouth of the Chicago River. Its ideal geographical location made it a vital link in the great waterway, and later on, with the expansion of railways, Chicago was transformed into the country’s railway hub. The rise of the city was not all smooth sailing, as in the Great Fire of 1871 about one-third of Chicago was destroyed. But it rose from the ashes like a phoenix and made itself a global center for finance, commerce, industry, transportation, and tourism.

Chicago boasts a diverse variety of tourist attractions, for example, every year tens of thousands of visitors come to the city just to marvel at its impressive and iconic buildings in postmodernist and gothic revival architectural styles. But it is not just the architecture that attracts people to the city by the lake. There are endless unique and fun experiences to be had here, such as enjoying the classic rides at Navy Pier, overcoming your vertigo at 360 Chicago Observation Deck, getting to know the urban art scene on a street art tour, and soaking in the sun and skyline on a cruise. If after all that excitement you want to escape to nature, Garfield Park Conservatory, Chicago Botanic Garden, and the Morton Arboretum are your best bet.

A trip to the United States is incomplete without visiting Chicago, the most American of American cities. But visiting a new city for the first time can be intimidating. Here are some useful tips for first-time travelers. When’s the best time to go? Spring is one of the most pleasant times to visit, but mid-March to mid-April is also the peak tourist time. Alternatively, give Fall a try as the weather is still mild but everything is less crowded. While Winters are freezing, but you’ll get the best deals on hotels and airfares (January and February).

Next up, where to stay in the city? With 50 districts or wards in the City of Chicago, choosing the right location for your trip depending on the purpose of your visit and budget. For first-timers, Chicago Loop or Chicago Downtown is where all the top attractions and countless dining options can be found. If you want to party the night away, the River North area is where the coolest nightclubs are located, plus it’s close to the Magnificent Mile. If you are on a budget or with a family, consider the lovely neighborhood of Lincoln Park.

Lastly, how to navigate around the city? Chicago has one of the largest and most convenient public transportation systems in the US, visitors should take full advantage of these affordable modes of transport to get around town. For a fare of $5, visitors can reach both of Chicago’s airports in under an hour by using the L trains. If you plan to use the public transit system a few times during your visit, save some hassle and money by getting a Ventra card for discounted fares or a multi-day pass for unlimited rides. For those who prefer to drive, download the ParkChicago app for all your street parking needs, rates vary by neighborhood and permit-only parking streets are marked.

Visitors traveling to Chicago have the luxury of choosing between two international airports – Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Both airports operate international flights, are equipped with state-of-the-art facilities, and have easy transfer options to the city.

Situated on the northwest side of Chicago and 23 km (14 miles) away from downtown, O’Hare International Airport is the larger of the two airports and one of the handfuls of major immigration gateways into the US. There are four terminals, with Terminals 1, 2, and 3 operating domestic flights, and Terminal 5 for international flights.

By far the easiest and most affordable way to travel between ORD and Chicago city center is via public transit. Blue Line trains provide service to O'Hare Airport via the O’Hare Station, which is located in the lower level of the concourse connecting to T1, 2, and 3. T5 passengers need to first use the free airport shuttle train. Fare costs $5, visitors will reach downtown in 40-45 minutes. Those who prefer to get a taxi should head to the official Taxi Stands at the lower-level curb front at each terminal. Make sure the taxi is metered and an average fare from O'Hare to downtown is $30-40.

Chicago Midway International Airport is located in the southwest part of the city. The airport has only one terminal and is about 16 km (10 miles) from downtown. For transfer options, visitors can use the public transit Orange Line trains which provide service directly between Midway Airport and the downtown Loop. For a one-ride ticket of $5, visitors will reach the city center in 20-25 minutes. For taxis, visitors can head to the official Taxi Stands on the lower-level curb front of the terminals, and an average fare from Midway to downtown is $35-40.

As the third-largest city in the United States, Chicago is an extremely accessible city for tourists. The Chicago Transit Authority (CTA) operates the second largest public transportation system in the country with eight ‘L’ train lines and 129 bus routes. Visitors get to ride the trains above-ground, at street-level, and underground too. Two lines operate 24/7, the Blue Line (Chicago O’Hare International Airport to downtown) and the Red Line (connecting North and South Sides via downtown). Visitors can buy a basic fare for $2.50, or get a Single-Ride Ventra Ticket for $3 as it’s good for up to 3 rides within 2 hours of use. To purchase the tickets, opt for a paper Ventra Ticket from the vending machine at every station, pay with a reloadable Ventra Transit Card, or get an Unlimited Ride Pass.

With roughly 130 bus routes, Chicago's city buses cover areas that the L trains don't. The fare costs $2.25, or $2.50 if you want a transfer, and remember if you change from an L train to a bus it costs an extra $0.25. Getting a Ventra card will save you some hassle and time as you’ll need to pay the driver with the exact change. Buses are particularly useful for attractions like Museum Campus, Hyde Park, and Lincoln Park Zoo.

If you want to head out to the suburbs, the Metra commuter trains have 12 routes from four terminals around the Loop. Fares are determined by the number of zones you travel through, so it can range from $4 to $11 for a single journey. Taxis are easy to find within downtown, and the fare begins at $3.25 for a metered ride and costs $2.25 per mile.

Chicago has a typical continental climate which means cold winters, warm summers, and four distinct seasons. Spring and Fall are the best times to visit the city, as in these months (April through May and between September and October) tourists will find the weather to be desirable, and crowds and prices are still manageable. Summer in Chicago is hot with moderate humidity, but it is also the peak tourist season too. Hence visitors should expect the highest lodging rates and packed crowds. In contrast, Winter in Chicago is bitterly cold and snowy, but if you don’t mind the big freeze, it’s also the season with great hotel and airfare deals.

As Spring is one of the most pleasant times to visit Chicago, mid-March to mid-April is also the peak tourist time for the city, the same goes for summer (from Memorial Day to Labor Day) and the winter holiday season (mid-November to early January). To avoid the crowds, give Fall a try as the weather is still pleasant but everything is less crowded. The best period for good deals is in January and February when hotel room occupancy is at its lowest, as result expect great savings and discounted prices.

From towering skyscrapers to renowned public art, from beautiful beaches to enormous greenhouses, Chicago is a metropolis that can keep visitors entertained no matter their taste.

For art lovers and history buffs, Chicago has some of the most distinguished museums in the world, such as the Field Museum, Museum of Contemporary Photography, Smart Museum of Art, and Chicago History Museum to name just a few. And the most admired of them all is the Art Institute of Chicago with its approximately three hundred thousand artworks. Visitors will be immediately impressed by the stateliness of this historic building when they walk past the pair of majestic bronze lions outside the museum. Inside, thousands of paintings, prints, photography, sculpture, and ornamental arts line the walls of various galleries and halls.

One of the best places to enjoy the great outdoors in downtown Chicago is Millennium Park. Not only is this an amazing green space in the middle of the city, but it also is the home to several pieces of famous public arts, such as the iconic Cloud Gate or known affectionately as "The Bean". This photogenic centerpiece has a mirror-like stainless steel surface that reflects the surrounding landscape as well as the tourists who walk through its central arch. Other notable attractions in the park include the Crown Fountain, Pritzker Pavilion, and Lurie Garden.

The urban landscape of downtown Chicago will not be the same without its stunning river and lake. Hence on a nice sunny day, visitors should take advantage of the river cruises, shoreline walks, and water sports on offer. Admire the awe-inspiring architectures along the Chicago River by taking a stroll or grab a bite to eat at the pedestrian-friendly Chicago Riverwalk. Along this scenic promenade, visitors can take it easy in one of the many restaurants and cafes, enjoy some live performance, or hire a boat or kayak and head out for an adventure on the river.

The culinary scene in Chicago is not just world-famous, but it is reputed for inventing some of the most beloved foods in the region and the world. From chocolate brownie, chicken vesuvio to Italian beef, foodie-travelers are in for a treat in the windy city.

The number one signature Chicago dish is the deep-dish pizza or Chicago-style pizza. Reportedly invented in Chicago in 1943, deep-dish pizza has a crust that is so deep, it resembles a pie rather than a flatbread. While visitors can find this local favorite in most pizzerias and restaurants, check out these highly recommended options: Pequod’s Pizza, Lou Malnati’s Pizzeria, and Giordano’s.

Another local favorite is the Chicago Italian Beef Sandwich. Originated in Southern Illinois, this hearty and delicious sandwich is stuffed with seasoned roast beef, sautéed green bell pepper slices, and giardiniera. These juicy and meaty bread parcels can be sampled at Roma's Italian Beef & Sausage, Al's Italian Beef, and Luke's Italian Beef.

Last but not least, the Chicago-style hot dog. This local creation of the all-American dog is a steamed beef hot dog in a poppy seed bun, topped with yellow mustard, bright green relish, onions, tomato wedges, and sport peppers.

Shopping in Chicago is a treat in itself. Being one of the iconic metropolises in the US, it’s no surprise that shopping fans visiting the city will be in their element with the finest museum shops, eclectic boutiques, and luxury shopping malls. What to get as a souvenir that is undeniably Chicago? Here are some favorite buys: Chicago skyline snow globe, Tiffany Elsa Peretti bean pendant, Frank Lloyd Wright memory game, 2930 Al Capone special edition armored Cadillac model, and Chicago ties.

As far as shopping goes in Chicago, it doesn’t get any bigger or more famous than the Magnificent Mile in the city center. Situated in downtown Michigan Avenue between the Michigan Avenue Bridge and Oak Street, visitors can shop their way through over 460 retailers from prestigious department stores (e.g. Macy’s, Nordstrom, and Bloomingdales), to world-class shopping centers (e.g. 900 North Michigan Shops, Water Tower Place, and The Shops at North Bridge).

Besides major shopping centers, locals adore their neighborhood independent retailers and boutiques. If visitors get the chance to explore the suburbs and quaint nearby towns, consider supporting the small businesses in Lincoln Park (historic park, zoo, and Victorian row houses), Andersonville (Swedish galore from shops, eateries to museums), and River North (gallery district with top range art, furniture, and home décor).

As the 3rd largest city in the US, Chicago has its public safety problems, but it is generally safe to visit for tourists. With a medium level of overall risk, tourists need to take precautions and be aware that certain neighborhoods need to be avoided. Pickpockets and bag snatching are common issues, so take extra care on public transport and leave your valuables in your accommodation. For emergencies, dial 911 for police, fire brigade, and ambulance services.

Like elsewhere in the United States, the US Dollar ($ or USD) is the official currency. Tipping is hugely important in the US, the standard tip in the country between 15-20%.