Whether you have just two days in Chicago or a little longer, there are more than enough things to do in Chicago to fill your itinerary. The Windy City is home to world-class museums, theatre, delicious food, plenty of shopping, and our fair share of tourist attractions. While I highly recommend adding a good dose of some of Chicago‘s popular attractions to your agenda, as a local I had to share some of my favourite places in the city.
Local Midwestern crooners, Miles Nielsen and the Rusted Hearts, performing at the intimate venue space in Schuba’s Tavern, which is located in a former Schlitz Tavern. Image © Brittany Lillegard
How to Spend Two Days in Chicago
Chicago’s Live Music Scene
Chicago is a city of music lovers and between the multitude of venues and summer festivals such as Lollapalooza, Blues Festival, Pitchfork and others, there is guaranteed to be a show during your stay, that will get your ears buzzing. When I’m home though, you will likely find me at one of my two personal favourite venues: Schuba’s or The Green Mill.
Schuba’s Tavern | 3159 N Southport Avenue
Not being one who is fond of large crowds, the intimate space at Schuba’s is the perfect venue size for me. In addition to a cozy space, The Schuba brothers are well-known around the city for sourcing some of the best acts in music to play at their venues (they also have a second, larger location called Lincoln Hall), and I can never say no to a pre-dinner Mac and Cheese and PBR at the restaurant at the front of the venue. The building itself is a former Schlitz Tavern, which is also a nice little slice of Chicago history.
The Green Mill | 4802 N Broadway Avenue
If you want to take a step back into the days of the Chicago mob, then this venue which was a favourite of well-known gangster, Al Capone, is a must visit. The jazz and cocktail club still has a lot of its original charm, and ordering a Manhattan to sip alongside one of the nightly jazz acts or poetry slams is always a good way to spend the evening. Insider’s Tip: The lounge doesn’t serve food, but the small, no frills taco stand around the corner is a great place to grab a quick bite before the show. If you are a bold eater, I happen to think this taco stand serves the best Lengua tacos in town.
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Known for having one of the most recognizable skylines in the world, Chicago’s ample outdoor spaces will give you multiple vantage points for taking in the tall architecture of the city. Image © Brittany Lillegard
Chicago’s Architecture
Home to the world’s first skyscraper and one of the tallest and most well-known skylines in the world, Chicago is an architecture lover’s paradise and narrowing down my favourites was a tough task. The Willis Tower, which was the tallest building in the world for twenty-five years, frequently makes it on every traveler’s list, but you should know that the locals still stubbornly refer to it by its former name, The Sears Tower.
I didn’t include it on my list of must see locations, because personally, I prefer the view from the Signature Lounge at the top of the Hancock Tower (and the fact that I can take in the views while enjoying a cocktail). Insider’s Tip: If The Sears Tower is on your must-see list though, I highly recommend purchasing tickets in advance to save yourself some time in line.
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The ceiling of the Rookery lobby, designed by Frank Lloyd Wright, is an excellent example of Chicago’s well-known architecture. Image © Brittany Lillegard
Rookery Building Lobby | 209 S. Lasalle Street
I have been inside the lobby of the famous Rookery building more times than I can count, and the interior still romances me as much as the first time. Designed by the famous Burnham and Root firm in the late 1800’s, the lobby was remodelled by Frank Lake Wright a few decades later and it is an impressive example of why Chicago is so well-known in the architecture world. You can take in the delicious light that is captured on the lobby on your own, but you won’t be able to go past the main entrance without booking a tour. Thirty minute guided tours can be booked through the Frank Lloyd Right Trust here.
Optimo Hats is one of the many artisan shops housed in the first floor of the Monadnock Building, where the preserved architecture will transport you to a different era. Image © Brittany Lillegard
Monadnock Building | 53 West Jackson Boulevard
Admittedly, the exterior makes it a bit easy to walk past the Monadnock without blinking an eye, but once inside, brace yourself to be transported to decades past. Constructed in the late 1800’s by Burnham and Root, only the first floor is open to the public but you can spend quite some time taking in all of the preserved architectural details.
Home to several companies that are keeping their craft old school, you will be able to pick out the perfect wool fedora, custom design the perfect suit, get an old-fashioned shave at the barber’s, or take a break to read the news while getting a shoe shine.
For a refreshment break, you can also get a hand poured coffee in the Intelligentsia Coffee Shop where the suspender-clad baristas dress the part, or belly up to the bar in Cavanaugh’s, where you are likely to run into locals enjoying an after work happy hour.
A beautiful curved doorway on one of the many mansions that lines Astor Street. Image © Brittany Lillegard
Astor Street | Few blocks west of Lakeshore Dr between Division St and North Blvd
Lining both sides of Astor Street you will find several remarkable 19th century mansions that have been home to many of Chicago’s elite over the city’s colored history. It is well worth spending a few hours taking a leisurely stroll down the street, but make sure to keep your eyes wide open so as not to miss the many small architectural details that make these homes so impressive.
You will find some early Frank Lloyd Wright touches on this street, as well as unexpected surprises like a well-preserved wooden alley from the early 1900’s. In the area, you can also stroll past the original Playboy mansion (1340 N State Pkwy) or finish your walk with an afternoon tea session at the Drake Hotel which is well-known for its famous neon pink sign as well as the many famous guests it has been privy to host including Princess Diana, Frank Sinatra, and Winston Churchill to name a few.
After all of the walking you will be doing, a stop at the Shoe Hospital, located in the Monadnock Building, will give you an opportunity to rest your feet and give your shoes a face lift. Image © Brittany Lillegard
Outdoor Spaces and Parks
The 606 Trail | Multiple Entrances
The 606 Trail is 4.3 KM of old elevated train tracks that have been repurposed as an outdoor trail space and public park. If you want to explore the city while being active, this relatively new space happens to be my favourite way to do so and is continually transformed and improved year after year. You will find both running tracks and ample space to bike with skyline views, art installations, and beautiful landscaping along the path. If you need a quick break, make sure to check out one of my favourite coffee shops, Ipsento 606, located just off the Milwaukee exit.
The 606 Trail, a former elevated train track transformed into a public outdoor space, offers 4.3 KM of running and biking trails where you can take in classic city views while getting in your workout for the day. Image © Brittany Lillegard
Chicago Lakefront Trail
Being inland, people tend to forget that Chicago is home to several beaches and an extensive lakefront trail (29 km to be exact) thanks to its location on the impressive Lake Michigan. If it is a good weather day, you can guarantee that locals will be flocking to the beaches and taking advantage of the lakefront paths.
For some of the best city views, I recommend starting at the south end at Northely Island Park, following the trail north around the museum campus, and continuing to head north towards Lincoln Park. Whether you decide to bike, run, or walk the path, this is one of the best ways to take in the skyline.
Garfield Park Conservatory
As one of the largest conservatories in the US, this free attraction is one of my favourite stops in Chicago. Home to multiple indoor and outdoor gardens and frequently called “landscape art under glass”, the architecture is just as impressive as the gardens housed within. While open year round, I highly recommend visiting during the summer months when you can also take in the outdoor gardens that span nearly twelve acres of ground.
Essential Acupuncture’s waiting room is a sleek and inviting space that will make you feel zen even before you have received your service. Image © Brittany Lillegard
Where to Pamper Yourself in Chicago
The best way to explore the city is definitely by foot, even if you only have two days in Chicago. But, it’s very possible that after so much eating and walking, you’ll want some time to relax and unwind. Below are my favourite places in the city to bliss out after a day of exploring.
Allyu Spa
Once you enter the doors of Allyu Spa you will forget that you are in the middle of a sprawling urban city. You can’t go wrong choosing any of the bodywork or skin care services that Allyu has to offer, but make sure to get to get to your appointment early so you have ample time to enjoy your complimentary tea in the meditation room, which in my opinion, is the most zen space in all of Chicago.
Essential Acupuncture
In addition to acupuncture, you will find a wide variety of holistic services here including cupping, gua sha and classic Chinese herbalism. On your first visit, you can expect a consultation to determine the best treatment for your needs and all services are warmly delivered by the passionate and knowledgable owners, Siri and Leigh. The perfectly minimalistic space is both welcoming and calm, so don’t be surprised if you find yourself wanting to return for multiple services during your Chicago visit.
Intuit Massage and Healing
Being one of my favourite self-care routines, I have had quite a few massages in my life, and Cameron of Intuit Massage happens to have the most magical hands I have come across in entire world. Her extensive knowledge of the human body coupled with her experience in blending both eastern and western massage techniques will leave you feeling blissed out and wishing you had booked the maximum massage time possible.
In addition to bodywork, Cameron also offers energy work to help you fully realign your mind, body, and spirit. Insider’s tip: Intuit Massage just so happens to be based in Essential Acupunctures space, so for a truly blissed out evening, I recommend booking an acupuncture session with Essential right after your massage.
Float Sixty Chicago
Life in the urban city can be hectic, but you will feel like you’re walking on clouds after just one session in Float Sixty’s sensory deprivation tanks. Floating involves immersing yourself in a small tank of body temperature salt water without any external noise or light providing the floater with an unparalleled meditative experience.
If you are not ready for a full-blown sensory deprivation experience, Float Sixty Chicago offers multiple options to test out the waters including larger rooms with ambient lighting and sound options as well as two meditation rooms that can be used before and after your experience.
In addition to multiple sensory deprivation tank options, Float Sixty Chicago also offers two meditation rooms where you can reflect on your experience or leave notes for future floaters. Image © Brittany Lillegard
Brittany is a traveling strength coach and yoga instructor from Chicago. She fuses her travel stories with her coaching background to help inspire and empower women to get comfortable with being uncomfortable, and to take charge of creating their own adventures.
She thrives off of coffee and wine, prefers to spend her days barefoot, and when she isn’t coaching or working on her handstand skills, she can be found plotting her next adventure.