48 Hours in Chicago Alone – Vol. 3

I’m excited to share the latest installment of my new blog series, 48 Hours in Chicago Alone which offers my picks for having a fun and diverse experience in The Windy City when you only have two days to explore on your own.  Don’t be shy because the good people of Chitown are amiable and they are ready to show you a great time even when you are flying solo.  Let’s head out!



Day 1 – 48 Hours in Chicago Alone – Vol. 3



Start your time in Chicago alone by grabbing breakfast or lunch at Eleven City Diner in the South Loop.  At this old-school Jewish deli you will enjoy huge omelets, excellent bagels, lox and much more.  In fact, breakfast is available all day, in addition to the superb matzo ball soup and burgers.  Sit at the counter at order an ice cream sundae or malted milkshake while taking in the kitschy memorabilia.




Chicago alone Eleven City Diner

Eleven City Diner in Chicago’s South Loop



Once you’re fat and happy, walk over to

Museum Campus and take in the history of the Field Museum, Shedd Aquarium, and the Adler Planetarium.  If you happen to be visiting Chicago alone during the summer, check out Jazzin’ at The Shedd on Wednesday nights where you can ogle the fish while sipping cocktails and listening to cool jazz bands overlooking Lake Michigan.




Chicago alone Shedd Aquarium at Museum Campus Jazzin' at The Shedd




Chicago alone Shedd Aquarium at Museum Campus Jazzin' at The Shedd



PRO TIP:  Read my article about How to Overcome Your Fear of Dining Out Alone.



When you’re hungry for dinner, hop on the Brown Line to Old Town (Sedgwick ‘L’ stop) and check in at The Vig.  Whether you sit at the bar or a table, the menu and craft cocktails will satisfy you in this stylish restaurant in the heart of Chicago. 




Chicago alone The Vig in Old Town

The Vig in Old Town, Chicago




Chicago is well known for its stand-up comedy and sketch comedy.  Luckily, Old Town is home to Zanies Comedy Club and The Second City where so many of America’s famous comedians and actors graduated to Saturday Night Live and movies.  Everyone should experience a few laughs while in The Windy City.  




Chicago alone Zanies



PRO TIP:  Check out my article, “Who Goes to a Comedy Club Alone?”



Chicago alone The Second City

Photo credit: The Second City



After you get your laughs on, top off your night and first day in Chicago alone at the historic Old Town Ale House which dates back to 1958.    Make sure you check out the naughty paintings on the walls and see how many famous faces you can identify.  This bar is not a fancy place but, instead, a tried and true dive bar of great importance to the city of Chicago.  It should most definitely be on your to-do list.




Chicago alone Old Town Ale House

Photo credit: Old Town Ale House



You should also check out my article about the 11 Chicago Bars You Absolutely Must Visit.




Day 2 – 48 Hours in Chicago Alone – Vol. 3



The coffee culture in Chicago is vast, and every neighborhood has its share of local coffee roasters’ blends as well as some imports from the east and west coasts.  Leave downtown and head up to Lakeview on the Red ‘L’ (Belmont ‘L’ stop) for a morning jolt of java at Osmium Coffee Bar which is on my list of the 30 Coolest Chicago Coffee Spots.




Chicago alone Osmium Coffee Bar



PRO TIP:  Read my article about the 7 Reasons Solo Travel is Good For You.



Perhaps there is no more fabulous sports town than Chicago.  When I first moved here twelve years ago from New York City, I couldn’t believe how fanatical and invested this city is about its sports teams.  The clerks in the supermarkets dress up in jerseys and hats for the Cubs, the Bears, and the Blackhawks.  Bars are packed for home and away games.  Chicago’s skyline is lit up in its teams’ colors.  Even if you’re not a huge sports fan, the camaraderie and team spirit here are highly contagious.    In 2016, the Chicago Cubs won the World Series, and this town nearly lost its collective mind.  The scene outside of Wrigley Field and at the city-wide parade for the Cubs for the week that followed was insane.  I highly recommend that you take of tour of Wrigley Field in Wrigleyville (Take the Red Line to the Addison ‘L’ stop).  Then, head over to Cubby Bear for a drink or two.




Chicago alone Wrigley Field




Chicago has so many stellar restaurants from which to choose so skip the iconic steakhouses and head out for a colorful, Spanish meal at Tapas Valencia in the South Loop.  I have been coming here for a few years, and the food never disappoints.  This spot is friendly, and there is a flamenco show on Saturday nights with Spanish guitarist.




Chicago alone Tapas Valencia

Tapas Valencia in Chicago’s South Loop




In addition to sports and comedy, Chicago is home to the blues, jazz, rock and other great music.  End your 48 hours in Chicago alone with a visit to House of Blues Chicago.  Whether you secure tickets for a large show in the very cool central space or a more intimate gig in the restaurant, you will be ending your solo vacation on the right note!




Chicago alone House of Blues Chicago

Photo credit: House of Blues Chicago



If you cannot secure a ticket at House of Blues, check out these other 21 Awesome Chicago Concert Venues.  You cannot go wrong.



I hope you enjoyed this short itinerary for some alone time in Chicago.  Check out more of 48 Hours in Chicago Alone – Vol. 1 and Vol. 2.  If you are considering solo travel in Europe, check out my articles, Who Goes to Venice Alone and Exciting Reason that Will Make You Visit Barcelona Solo.