Tips only locals know about visiting Chicago

What locals appreciate most about their beautiful city is the architectural history that its streets hold, its world renowned monuments, and its world-class lake-side advantage.

Chicago’s skyline includes old, architecturally rich buildings that are worth seeing in person, such as the Chicago Board of Trade, the Tribune Tower, and the Chicago Opera House. In particular, Chicago’s Tribune Tower truly sticks out from the rest of the rather modern skyscraper landscape as it offers unique neo-gothic features and is surrounded by smaller sized buildings. For context, the Tribune Tower was home to the newspaper of the same name and a media and broadcasting hub used for publishing and radio. Most interestingly, the tower was built in 1925 after a $100,000 design competition in 1922 claiming New York architects John Mead Howells and Raymond Hoof the victors. Heavily inspired by the Rouen Cathedral in France, this choice of Late-Gothic style architecture was definitely original to the scene but successfully accepted by Chicagoans!

Apart from the famous Cloud Gate, a Chicagoan favourite is the Tiffany Dome, the largest one of its kind in the world, located in the Chicago Cultural Center.

This breathtaking art glass dome was last redesigned in 2008 out of 30,000 pieces of colourful glass in a 200-foot-diameter cast iron frame. This gold-themed and innovative structure allows the cultural centre to be bathed in natural light, thus saving electricity and energy.

On a more historical note, Chicago locals love to parade around the Navy Pier, most notably known for its purpose during the first and second world wars. It served as a military base for navy personnel during WWI, whereas it concentrated more on pilot training for over 15,000 fighter pilots during WWII. Finally, the Navy Pier also served as a housing location for soldiers and the Red Cross to aid those who served in the war effort.

It is a known fact that Chicago locals are loyal fans to their baseball team, the Chicago Cubs (also referred to as Cubbies). Indeed, having won three world series (1907, 1908, 2016) in the National Baseball League, there is a lot to boast about. Moreover, over the years, Wrigley Field, the Cubs’ homebase, was the location of historical baseball moments, such as Gabby Hartnett’s winning home run in 1938 against the Pittsburgh Pirates, helping the team reach the postseason status that same year.

So if you want to feel like a real Chicagoan, book your tickets amongst the locals on the bleachers at Wrigley Stadium as they cheer their excitement to the players! 

If you are the artistic type, the city's must-see attraction is the world renowned Art Institute of Chicago, recently awarded as one of the best US attractions this past year on Tripadvisor. You may have seen snippets of this museum in films such as the John Hughes classic, Ferris Bueller’s Day Off (1986). Indeed, this astounding institute has collected over 300,000 works of art with a wide variety of styles and from all continents spanning through decades (with pieces dating all the way back to Ancient Egypt). You may see its most proud possessions, such as  Edward Hopper’s Nighthawks (1942) or Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte (1884-1886). 

Note: The institute is closed on Tuesdays and Wednesdays.

A great way to learn the local lingo and Chicago humour is by attending one of their comedy club shows. And where else but where the greats started out? As you wander around the Old Town, it may be worth your time stopping by The Second City, a cabaret-style comedy club where world renowned actors/comedians started out their careers through improv (such as Tina Fey, Steve Carell, Bill Murray, or Stephen Colbert to name a few). Second City offers a unique interactive experience that will show you first hand why Chicago is considered one of the US most renowned cities for comedy and entertainment!

More of an architecture enthusiast? No problem. One of the best ways to see Chicago is to cruise its river and marvel at its historical architecture. There are many guided tours to choose from, but the Shoreline Sightseeing Architecture River Tour offers a first-class architecture-focused commentary when passing by major monuments. So sit back, relax, and take in the views whilst breathing in the breezy air of Lake Michigan. 

If you are looking for that extra-edge, you should look into visiting the 360 Chicago Observation Deck. Observe the Magnificent Mile and its surroundings at a height of 1,000 feet! The particularity of this observation deck is that it is tilted, giving even more exposure to a never-before-seen view of all Chicago. But beware, if you are afraid of heights, this may be your worst nightmare. Celebrating an occasion or your trip? Grab a drink at the CloudBar. Looking for a more casual and cheaper alternative? Check out Willis Tower’s 103rd floor Skydeck and Tower Ledge experience using your Chicago EasyPass available here. 

All you music enthusiasts out there must be dying to know where you can listen to Chicagoan Blues. Well, we have the answer you’re looking for. Book one of your evenings at Buddy Guy’s Legends blues bar - a retro venue located at 700 South Wabash Ave. This bar invites the most talented artists in jazz and blues from all over the US while serving guests drinks and/or a meal in a truly spectacular atmosphere. 

Although quite central and vibrant, there is a reason most locals retreat to the Loop district for dining, drinking, and shopping. Conveniently located in downtown Chicago, the Loop district is most known in movies for its high-rise metro lines that circle the district buildings. Indeed, it is Chi-town’s commercial core, but it is still extensively used by locals and worth seeing in its naturally buzzing environment. Wonder around the impressive skyscrapers, stop by boutiques or a coffee shop and mingle amongst the locals!

Get lost in Chicago’s Brooklyn-like neighbourhood just north of Milwaukee Avenue: BuckTown. Discover the history behind Polish-style cathedrals and walk along the charming brick buildings of this village-like neighbourhood. Having gentrified considerably over recent decades, the area around Wicker Park in particular is submerged with yummy trendy restaurants and elegant dive bars. A local’s tip: make a stop at Margie’s Candies, an old-fashioned American candy shop nestled in the corner of Armitage and Western Avenues. Marvel at shelves packed with endless selections of delicious candies and chocolates for all to enjoy! 

Finally, visit the new home of the hipsters: Logan Square. Culturally enriched with various communities (such as norwegian-americans, latinos, poles, and the new millennial generation) housed in bungalow-style homes, Logan Square area is youthful and artistic. Indeed, the lakefront communities that migrated to this district after inflation have led to more creative initiatives such as the development of colourful coffee shops, bars and restaurants as well as communal green projects!

The most central and easy-access places to grab a bite to eat or dine-out for a date is on West Randolph Street, located in the West Loop. Heavily frequented by locals, this avenue hosts every type of food desires you may have with a flexible range of prices and establishments depending on your mood. Indeed, you may bump into a mix of crowds - from upper-class businessmen and women enjoying post-work drinks to local couples dining out to their favourite local joint. Fun fact: this is where Oprah Winfrey first lived when she started her show back in 1986 and has been increasingly popular ever since!

If you’re looking for a festive night out, you must reach Clark Street and its never-ending bar strip. From traditional Irish pubs, to trendy underground dive bars, there is a place for everyone. From working class professionals to students living up the happy hour at a lower-end yet fun-packed bar, you are guaranteed an eventful evening wherever you may land. Locals highly recommend you pub crawl until you find your cup of tea on one of the liveliest streets in all of the United States!

To save time in hotel searching, here are a few suggestions of places to stay in the neighbourhoods mentioned above:

If you are looking for centrality and practicality, consider booking your stay at citizenM in Chicago’s buzzing Loop district. Located in downtown, this hotel offers an advantageous situation close to metros lines and surrounded by countless restaurants and shopping options. Enjoy bright rooms and colourful designs in this four-star gem that also accommodates a fully functional gym! 

Looking for some lake view action and a short walk to your next Cubs game? Well look no further and enjoy a comfortable stay at the Best Western Plus Hawthorne Terrace Hotel and its sublime brick architecture. Break a sweat at their gym or in their indoor pool in a cosy ambiance! Great for couples or families, these large rooms give you the space and peace one needs after a long day of travelling. 

Right by the Old Town and located in Lincoln Park, Hotel Lincoln is a classical all-American approach. With simple yet classy interiors and friendly personnel, you are guaranteed a delightful stay with the whole family. Enjoy dining from the comfort of your own room or amongst the other guests in the dining area, or perhaps a nightcap at the hotel lounge before you head to bed! 

Looking for that authentic Chicagoan experience? Book a room in Ray’s Bucktown Bed and Breakfast and mingle with the locals. It is undeniably charming and located on a quiet street - can’t get better than that! Bring home to you and enjoy luxurious perks such as a session at the spa bath. Walk out and wander the streets of a truly proud Chicagoan community. Who knows? Maybe you’ll be one of them some day!