7 Unique things to do in Downtown Chicago

by Paul Joseph  |  Published March 12, 2018

Known as The Loop, Downtown Chicago is at its most vibrant during the week when it hums with professionals going about their working days. But whereas weekends were once deathly quiet, in recent times the district has come alive out of office hours too. The vast green expanse of Millennium Park, in the heart of downtown, is the scene of some of Chicago’s finest outdoor cultural events, including high-profile musicals and art shows, while several new residential towers now house the city’s large student population who bring a youthful energy to the area.

A view over the water towards downtown Chicago (Photo: عبدالرحمن القصيِّر via Flickr)

Downtown Chicago has a distinctive vibe that sets it apart from anywhere else in the city. If you’re planning a visit, we highly recommend that you venture beyond its well-trodden path and explore some of its lesser known nooks and crannies. To help inspire you, we’ve picked out 7 of the best unique things to see and do here.

Plan your trip

Chicago’s downtown district has a huge choice of hotels, ranging from no-frills budget options through to the pinnacle of luxury. So whether you’re drawn to The Loop by the mouth-watering food, the pulsating nightlife or the vibrant cultural scene, you’re certain to find something that suits your needs. Check out our list of some of the best hotels to be found in downtown Chicago here.

1. Turtle Racing at Big Joe’s

If you’re craving entertainment of the ‘alternative’ variety, then Big Joe’s is guaranteed to satisfy your quirky predilections. Every Friday the bar hosts turtle races – yes, you read that correctly – and it is an event that attracts a loyal crowd who come to cheer on the shell-encased reptiles. The contests takes place on a special ring placed atop a pool table, with the turtles held under a clear container until the buzzer goes off. At this point the container is lifted and the race commences, with the first turtle to reach the outer edge of the ring hailed as the winner. To add a competitive edge to proceedings, patrons are assigned their own turtle by purchasing pitchers of beer.

LOCATION 1818 W Foster Ave HOURS Mon-Fri 1pm-2am Sat 12pm-3am Sun 12pm-2am

Turtle Racing at Big Joe’s

Turtles jostle for position ahead of a race at Big Joe’s (Photo: katiebordner via Flickr)

2. Merz Apothecary

This inconspicuous pharmacy a few miles north of downtown, where it also has a second store, has an intriguing past, dating back to a time when the prescription of medicines was very different from today. The store was opened in 1875 by a local pharmacist named Peter Merz, who would prescribe a variety of herbal medicines to relieve his customers’ ailments. But rather than call it a pharmacy, Merz followed the European tradition and named it an “apothecary”, and it soon became popular with European immigrants. Fast forward to 1982 and the store was moved to a larger building down the road, designed to resemble a turn-of-the-century apothecary, complete with a hand-carved wooden facade, tin ceilings, and oak cabinets. No longer just a one-stop-shop for natural health and classic European products, Merz is also a destination for niche fragrance, skin care, candles, men’s grooming essentials, and more, but its links to the past can still be found through the vintage apothecary jars lining the walls and the aroma of natural herbs that sifts through the air.

LOCATION 4716 North Lincoln Avenue HOURS Mon-Sat 9am-6pm Closed Sun

Merz Apothecary

The soap wall inside the historic Merz Apothecary (Photo: Merz Apothecary)

3. Join a walking Tour

There’s no better way to get to know a city than by walking around it, and as one of the most walkable cities in America according to surveys, Chicago is the perfect place to hit the streets and delve under its skin. If this takes your fancy, then Inside Chicago Walking Tours hosts a range of public and private tours themed around the rich and diverse architecture of the downtown district. The company’s founder, Hillary, whose, experience, enthusiasm, friendliness and knowledge create engaging and entertaining tours in equal measure, leads most tours herself. The tours typically last two hours and cover around a mile and a half at a leisurely pace, during which time you’ll visit a wide variety of buildings (both inside and out) and gain a deep insight into Chicago’s architectural heritage, all brought to life by Hillary’s fascinating stories. There’ll be plenty of photo opportunities along the way too.


Inside Chicago Walking Tours

A dramatic view of one of the so-called ‘secrets of the Loop’ (Photo: Inside Chicago Walking Tours)

4. Chicago French Market

Chicago is a mecca for food-lovers and one of the best places to head for sampling some of the city’s rich and varied cuisine is this bustling French market. Home to over 30 speciality vendors, the market features a huge variety of stalls selling French ingredients to take away as well as several dine-in venues and grab-and-go options too. Open all day, the choice here will blow your mind – as well as your tastebuds – with everything from meatball subs to lobster rolls, ceviche to empanadas, Belgian fries to mac n cheese, chocolate truffles to French macarons, and plenty more. There are also regular Happy Hour specials, live music, and monthly events, making it one of Chicago’s most vibrant and unique public spaces.

LOCATION 131 North Clinton Street HOURS Mon-Fri 7am-7.30pm Sat 8.30am-5.30pm Closed Sun

Chicago French Market

A mouth-watering assortment of delicacies at Chicago French Market’s Firenze Italian Street Food stall (Photo: Chicago French Market)

5. Hop on a bike tour

Another great way to experience Chicago is on a bike tour. With the wind in your hair, you’ll get to visit the neighbourhoods where locals live, work and play, while making the most of the city’s reputation as one of the best in America for cycling. One of the most popular companies for traversing Chicago’s flat terrain, vast network of sidewalks and trails, and expanses of green spaces aboard a bike, is Bobby’s Bike Hike, who run a range of cycling tours (among others), all of which deliver a unique insider’s view of the culture, history, architecture, and little known facts that define the iconic Windy City. Tours are themed around particular areas of interest, such as food and gangsters, and there are also kid-friendly Tike Hike tours, which take in more family-oriented sites along the way, such as a petting zoo.


Bobby's Bike Hike

Guests on a Bobby’s Bike Hike tour cycle along against the backdrop of the Chicago skyline (Photo: Bobby’s Bike Hike)

6. SafeHouse Chicago

Spies and double agents continue to hold an enduring fascination, and in Chicago there’s a venue dedicated entirely to the mysterious world of espionage. Safehouse Chicago is a themed nightclub and restaurant that’s awash with genuine spy-related artifacts, pop culture references and spy paraphernalia from top to bottom, including original props from James Bond movies. From the minute you locate its top-secret entrance – marked only by a small plaque next to a nondescript red door with a sign that reads “International Exports” – and pass the clearance test to prove you’re not a double agent, you’ll find yourself immersed in an authentic espionage experience. Open to ‘agents’ of all ages, this is without doubt one of the city’s most unique attractions. The food menu is great too, and be sure to sample some of the craft cocktails. There is even a secret exit (which is highly recommended) because a good spy never leaves the same way they came in.

LOCATION 60 East Ontario Street HOURS Sun-Wed 11am-12am Thurs-Fri 11am-2am Sat 11am-3am

SafeHouse Chicago

Patrons enjoying themselves in the atmospheric environs of SafeHouse Chicago (Photo: SafeHouse Chicago)

7. Lollapalooza

Founded in 1997, this annual music festival is one of the largest and most popular anywhere in America, attracting more than 150,000 revellers every year. Genres including alternative rock, heavy metal, punk rock, hip hop and electronica all feature, with some of the world’s biggest musical names having performed at the event, including Nine Inch Nails, Kanye West,The Smashing Pumpkins, Red Hot Chili Peppers, Queens of the Stone Age, Arctic Monkeys, Franz Ferdinand, Beastie Boys and Radiohead. As well as live music, the festival has also provided a platform for several political groups and visual artists down the years, including a small theatre troupe reciting poetry.



A stage performance during a previous edition of Lollapalooza (Photo: Mark Moschell via Flickr)