The Ultimate Guide To Downtown Chicago | Travel The Food For The Soul (2024)

Chicago, a quintessential city with a multitude of skyscrapers, museums, beaches, waterfronts, nightlife, sports venues, shows, and performances, offers a blend of stunning cityscapes and several cultures!

Renowned the world over for its amazing architecture and some of the tallest structures in the world, Chicago needs no introduction! Considered the birthplace of modern architecture, Chicago’s architecture and skyscrapers have inspired several other high-rise structures in other parts of the world! However, it’s not just the towering steel and concrete structures but also the well-planned parks, museums, waterfront, and shopping districts throughout the town that make Chicago one of the most sought-after destinations in the US!

Once home to the Native Americans, Chicago has seen some significant and fast-paced development, despite the devastatingGreat Chicago Firethat caused a lot of damage to the city in 1871. However, nothing could stop Chicago from growing, and soon several industries, including transportation, manufacturing, advertisem*nt, and commerce, flourished in the city and attracted several immigrants from all over the globe. Making Chicago one of the most culturally diverse cities in the US!

Located in northeast Illinois, on the shores of Lake Michigan, Chicago is also popularly known as the Windy City due to the year-round lake breeze coming off Lake Michigan. Lake Michigan also gives Chicago its waterfront and beaches, and the Chicago River, flowing through the city amid the towering building, gives Chicago its unique canal system and water taxis. However, Lake Michigan is also responsible for the harsh winters and snowfall in Chicago, making Chicago a less desirable destination during the winter months.

Chicago has endless sightseeing opportunities, complemented with a few excellent land and river tours offered by a few tour companies!

Chicago is one of the most popular tourist destinations in the world, featuring several architectural wonders, world-renowned museums, a state-of-the-art planetarium, waterfront recreational activities, diverse neighborhoods, live performances, shopping districts, and some of the best culinary experiences. However, there’re a few great tour options, including narrated bus and boat tours, that make it pretty easy to navigate the city and explore the several attractions in Chicago.

Directly flying into Chicago international airport and staying in downtown Chicago is the best way to explore the city!

Best Time To Visit Chicago: Summer is the busiest season in Chicago, with warm temperatures ideal for waterfront and outdoor recreational activities. However, summer’s also the time when you’re most likely to stand in long queues to get inside a museum or an attraction. If you don’t mind slightly cooler weather, visiting in spring and fall is a great option to beat the crowd in Chicago. Winter is harsh with regular snowfalls and is not the best time for outdoor activities, but there’s a ton of indoor things to do in Chicago that can be enjoyed during the winter months too.

Time Required AtChicago: With so much to see and do in Chicago, I recommend spending a minimum of two days to see the city’s major highlights. However, if you have more time, you could spend an entire week exploring every museum, multiple neighborhoods, take various tours, enjoy some of the great shows, and of course, indulge in some of the best cuisines and restaurants in Chicago.

Getting To Chicago: The best and most comfortable way to get to Chicago is by flying into Chicago O’Hare International Airport, located very close to downtown Chicago. Alternatively, you could also take a train or a bus to Chicago.

• Flight: Chicago O’Hare International Airport is the closest airport to downtown Chicago and is serviced by several airlines. Located about 20 miles from the downtown, O’Hare International Airport (ORD), Chicago, Illinois, is the best airport to get to Chicago.
• Train: Chicago Union Station, located in downtown Chicago, connects several cities and states to Chicago and is also a major hub for several train networks in the US.
• Bus: Greyhound offers bus services to Chicago, with the closest Greyhound bus stop located in Harrison Street, right next to downtown Chicago.

Parking & Transportation In Chicago: Most hotels and attractions in Chicago offer paid parking, and there are quite a few public parking lots in the downtown area. However, if you’re flying into Chicago and staying in the downtown area, which I highly recommend, you really don’t need to rent a car in Chicago. Traffic and finding parking can be challenging in Chicago, especially during the summer months, the busiest season in Chicago. Additionally, most of the attractions in Chicago are located close to each other and are better explored using public transportation, private cab, or a guided bus tour that takes you to all attractions.

Tours & Multi-Attraction Passes In Chicago: I highly recommend using a hop-on-hop-off tour service in Chicago so that you spend less time driving and finding parking and instead have more time at your destination. The best way to explore Chicago is by using theBig Bus Toursand purchasing a multi-attraction discounted pass fromCityPASSorGo City. You don’t have to buy separate tickets for the Big Bus Tours as it’s one of the attractions included in the Go City pass. A trip to Chicago is incomplete without doing theChicago Architecture Boat Tour, a narrated river cruise highlighting several architectural landmarks of the city.

Lodging & Dining In Chicago: Chicago is bustling with hotels ranging from boutique hotels to bread and breakfasts! Though there’re several places to stay outside the downtown area, I highly recommend staying in Chicago downtown for easy access to the attractions and an authentic Chicago experience. The dining options in Chicago can be overwhelming, ranging from fine dining to casual waterfront dining, but you must try a few popular Chicago dishes, including deep-dish pizza, Chicago hot dogs, and barbecue when visiting the town. I have reviewed the lodging and dining options in Chicago in detail in the later section of this post.

Other Attractions Near Chicago: Unquestionably, downtown Chicago is the main tourist attraction in the state of Illinois and should be on top of your list. However, if you’re done visiting all Chicago attractions and still have time or would like to take a break from the hustle-bustle of the city, I recommend visiting theBahai House of Worship, located about 18 miles north of downtown Chicago, andAnderson Japanese Garden, located around 85 miles northeast of Chicago.

The best way to explore Chicago is by using a hop-on-hop-off bus tour to get to the museums and landmarks and marveling at the grandeur of skyscraping structures on-board a boat tour!

Given the several sightseeing options, including numerous museums, parks, architectural landmarks, and waterfronts spread all over the town, driving and finding parking can be very time-consuming and can be a big challenge, especially if you’re traveling during the summer months. So, I highly recommend using one of the tour companies that offer hop-on-hop-off bus tours and river tours to get the most out of your trip to Chicago.

Hop-on-hop-off Bus Tours: The hop-on-hop-off narrated bus tours in Chicago are a great option to learn about the city’s history and culture and easily get around the city. There are a couple of tour companies that offer hop-on-hop-off bus tours in Chicago –Big Bus ToursandCity Sightseeing. These companies provide quite frequent busses, and I love that Big Bus also offers a phone app using which you could track the real-time location of the next shuttle.

River Cruises & Tours: There are several river & lake cruises offered in Chicago, starting from the Navy Pier and the River Walk area. The most popular being the Chicago Architecture Cruise offered by –Shoreline Sightseeing CruisesandCruise Chicago, departing from Navy Pier and River Walk. You could also enjoy Lake Michigan and Chicago’s skyline on-board one of thedining cruisesoffered at the Navy Pier.

Multi-Attraction Passes: Buying a discounted multi-attraction pass from CityPASSorGo Citycan really save you money and, most importantly time, that you would otherwise spend standing in queue to purchase tickets at each attraction.

End a hectic sightseeing day by watching a spellbinding show at one of many theaters in Chicago!

Chicago is home to numerous theaters featuring several entertaining shows, including concerts, live performances, stand-up comedies, musicals, and much more. Whether you want to see a Broadway show or a locally inspired play, you will find it in one of Chicago’s 250 theaters! Touring the downtown and marveling at the architecture in the daytime followed by dinner and a show is my idea about an ideal trip to Chicago!

There are about 250 theaters in Chicago that host shows and live performances by several renowned artists, bands, and production companies. The theaters in Chicago can be grouped into three major theater districts – Loop, Edgewater, and Belmont. Below, I have listed the most famous theaters in each district, along with the popular shows and links to the websites, where you can book your show tickets.

The Loop: The most popular theater district of Chicago, the Loop is home to some of the best and elegantly decorated theaters in the US, includingOriental Theatre,Cadillac Palace Theatre,CIBC Theatre,Auditorium Theatre,The Lyric Opera,The Goodman, andBroadway Playhouse. These theaters host some of the biggest shows, including Wicked, Hamilton, A Christmas Carol, Jesus Christ Superstar, and more.

Edgewater: TheEdgewater theater districtis a lakefront neighborhood that’s home to several independently owned stores and theaters hosting shows and performances of several theater companies, includingThe Neo-Futurists,Babes with Blades Theatre Company,Jackalope Theatre Company, andRaven Theatre.

Belmont: TheBelmont theater districtof Chicago, a large lakefront theater district, is home to several theaters that host stand-up performances and shows, including Blue Man Group, Bluebird Arts, Laugh Factory, The Newport Theatre, and others.

I highly recommend staying in downtown Chicago for easy access to the attractions and an authentic Chicago experience!

Hotels In Chicago: Staying in downtown Chicago has several upsides, including easy access to several attractions and tours, there’s no need to rent a car, and the liberty to enjoy late-night shows and nightlife. There’re several hotels in downtown Chicago, ranging from boutique hotels to bread and breakfasts. Here’re are my top picks for hotels in downtown Chicago

• Waldorf Astoria Chicago: Located in the heart of downtown Chicago,Waldorf Astoria Chicagois a luxury hotel featuring lavish guest rooms, spa services, and several dining options.
• Four Seasons Hotel Chicago: With easy access to Chicago’s shopping and theater districts, the luxuriousFour Seasons Hotel Chicagois an excellent lodging option in downtown Chicago.
• Hyatt Centric Chicago Magnificent Mile: TheHyatt Centric Chicago, located on the Magnificent Mile, offers contemporary rooms, excellent guest service, and a couple of on-site dining options.
• Chicago Marriott Downtown Magnificent Mile: Located on Michigan Avenue, close to the Magnificent Mile,Chicago Marriott Downtownoffers modern amenities, great views, and culinary experiences.

Restaurants In Chicago: The dining options in Chicago can be overwhelming, ranging from fine dining to casual waterfront dining; you will find every cuisine in Chicago! There’re so many eateries in every street of the town it’s impossible to try them all and pick one over the other. However, here’re a few dishes and joints you must try when in Chicago – Giordano’s deep-dish pizza, Chicago hot dogs, and Chicago’s famous barbecue ribs, sandwiches and shakes at Portillo’s, and mouthwatering Eli’s Cheesecake.

I hope you enjoyed reading the post, The Ultimate Guide To Downtown Chicago, and I hope this will help you plan your trip to Chicago. You can find other Illinois attractions in my Illinois Travel Guide.