48 Hours in Chicago Alone – Vol. 2

Happy Hump Day, Everyone!  I hope you are all settling into the new year well and you are contemplating some exciting travel plans for 2018.  Today, I would like to spread some Wednesday Wisdom about spending 48 Hours in Chicago Alone.  This is my second installment in this new blog series about solo travel in Chicago and I am excited to help you take the guesswork out how to spend just two days in The Windy City.  I know that sometimes you are only in town by yourself for a quick business trip or getaway so grab your bag, your sense of adventure and let’s head out!


48 Hours in Chicago skyline

Day 1 – 48 Hours in Chicago Alone – Vol. 2


Lou Mitchell’s is the historic diner that has been serving up comforting breakfasts and lunches since 1923.  It’s located slightly west of

The Loop on Jackson Blvd, one block south of where Route 66 begins on Adams St.  This place is the perfect spot to begin your 48 hours in Chicago and it opens at 5:30 am during the week.  Chicago has always been known as a hard-working town and people here need to fuel up before the sun comes up.  




48 hours in Chicago Lou Mitchell's

Lou Mitchell’s on Route 66



Once you’re finished getting your morning kicks on Route 66, hop the CTA Green Line up to Oak Park (Take the ‘L’ to the last stop, “Harlem”) and visit the Frank Lloyd Wright house and studio.  Tours are available or you can take your time strolling around the streets on your own. This beautiful neighborhood is filled with stunning architecture in the style of Wright who created the very recognizable and unique prairie-style houses.




48 hours in Chicago Frank Lloyd Wright Oak Park




After you’ve soaked up the architecture of Frank Lloyd Wright in Oak Park, celebrate your first dinner of your 48 hours in Chicago at Monteverde in the West Loop.  This Italian hot spot is helmed by former Top Chef contestant, Sarah Grueneberg who is just one of the many celebrity chefs in Chicago.  All of the hand-pulled pasta dishes are must-dos as are the seafood choices.




48 hours in Chicago Monteverde in the West Loop

Monteverde in the West Loop



I understand that many of you feel nervous or self-conscious about going out for a meal by yourselves.  It is a very common anxiety among solo travelers.  In preparation for spending 48 hours in Chicago, read my tips for How to Overcome your Fear of Dining Out Alone.



Now that Monteverde has you fat and happy, top off your evening with some live music at Andy’s Jazz Club in the River North neighborhood.  Chicago is home to the blues and there are several great options including Buddy Guy’s Legends.  However, if jazz is more your vibe, Andy’s Jazz Club is a popular spot to get groove your groove on.




48 hours in Chicago Andy's Jazz Club

Don’t be afraid to treat yourself to some great jazz during your 48 Hours in Chicago Alone.



PRO TIP:  Discover the 7 Reasons Solo Travel is Good for You



Day 2 – 48 Hours in Chicago Alone – Vol. 2



After you’ve had a good night’s sleep, start your second day in Chicago at Goddess & the Baker in The Loop.  Here you’ll have a delightful choice of coffee, tea, hot chocolate, pastries and more.  I love coming here in the morning and sitting solo for a while as I watch the hustle and bustle of people scurrying to work.




48 hours in Chicago Goddess and the Baker




48 hours in Chicago Goddess and the Baker

Goddess and the Baker in Chicago’s Loop



No trip to Chicago would be complete without taking one of the architectural boat cruises on the Chicago River and Lake Michigan.  I enjoy the docents on Chicago’s First Lady cruise ships.  Each time I hop on one of these tours during the morning, afternoon or at sunset, I learn something new about Chicago and it’s iconic skyline.  Whenever you are visiting a city surrounded by water, take advantage of the ability to see it from a different point of view.




48 Hours in Chicago Chicago's First Lady

Chicago’s First Lady Architectural cruise



After your architectural boat cruise, take a walk down Michigan Avenue and head to Millennium Park to see Cloud Gate (a.k.a “The Bean”), Crown Fountain and the other art sculptures in the gardens there.  During the winter, enjoy some outdoor ice skating or some exhibits at The Art Institute of Chicago which is adjacent to Millennium Park.  There is plenty right there to round out your afternoon.




48 Hours in Chicago Millennium Park Chicago Athletic Association Cindy's Roof Chicago during the holidays

The view of Millennium Park and The Bean from Cindy’s terrace



In the warmer months, take in the summer film series with wonderful acoustics on the great lawn by Pritzker Pavilion.



48 hours in Chicago Chicago concert venues Millennium Park

Millennium Park at Pritzker Pavilion has great concerts and a Summer Film Series




By now, you’ve probably worked up an appetite so hop on the Blue Line and head to Wicker Park for dinner at Piece Brewery and Pizzeria.  This is not that Chicago deep dish nonsense!  I never met a Chicagoan who admits to liking that stuff.  Instead, Piece serves lovely thin crust, New Haven-style pizza and more in a super fun setting.  If you stop by on a Saturday night at 11 pm, you can experience their live band karaoke.  




48 hours in Chicago Piece pizzeria

Photo credit: Piece Pizzeria



Chicago has one of the most stylish and hot cocktails scenes in the U.S.  After you’ve enjoyed some pizza at Piece, stay in Wicker Park and cap off your night at The Violet Hour.  This place is sexy but don’t let that stop you from stopping in by yourself and checking it.  It will be a wonderful way to end your evening in Chicago.




48 Hours in Chicago The Violet Hour

Photo credit: The Violet Hour



Before you head out of town, you may want to pick up a souvenir or two.  I prefer my solo travel memories in edible form so head over to one of the many locations of Garrett’s Popcorn downtown.  This iconic brand began in Chicago and there are several flavors to please your palate.  The caramel-crisp and cheddar combination is a fan favorite and you can ship tins of this stuff to family and friends.



48 hours in Chicago Garrett's Popcorn


There you have it, folks, 48 Hours in Chicago Alone – Vol. 2.   Check out my first installment of this new blog series for additional ideas about how to enjoy some solo travel in The Windy City.  Time wait for no one and neither should you.  Embrace solo travel!