48 Hours in Chicago Alone – Vol. 1

I’ve been calling Chicago my home for the last twelve years and I’ve written a considerable amount about it here on the blog.  So I thought it would be convenient to begin a series of articles with suggestions for spending only a couple of days here.  After all, big cities can be overwhelming with only two days to spare and you might not know where to begin.  That said, below is the first contribution to my new series entitled “48 Hours in Chicago Alone.”  I hope the solo travelers out there find my short itineraries useful because Chicago is a very friendly town with a Midwestern charm. You’ll feel right at home.



Chicago skyline 48 Hours Alone in Chicago

Chicago skyline



Day 1


Whether you arrive in Chicago by train, plane or automobile, you should

fuel up with some great coffee, pastry or lunch at Hendrickx Belgian Bread Crafter.



Hendrickx Belgian Bread Crafter 48 Hours in Chicago Alone

This chocolate croissant is so buttery!



This delicious spot is one of many Sensational Chicago Bakeries that Will Make You Drool.  Don’t miss the phenomenal, buttery chocolate croissant.  It’s so delightful.



Fans of blues and rock ‘n roll music will want to check out the legendary Chess Records (Blues Heaven Foundation)This music studio and museum is where Buddy Guy, Etta James, Muddy Waters and The Rolling Stones have recorded their iconic records.  Make an appointment any day except for Sunday and take a tour of the studio while you enjoy memorabilia from some of the music industry’s most famous artists.  Read more about my solo excursion to Chess Records.




Chess Records original studio instruments 48 hours in Chicago alone

Original studio instruments at Chess Records



While you’re on the near south side of Chicago, check out the very original craft beer at Moody Tongue Brewing Company.



Moody Tongue Brewing Company 48 hours in Chicago alone

That’s a blueberry Pilsner on the right!



This hot new spot has a tasting room with a fireplace where you can sip seasonal brews while enjoying their signature 12-layer chocolate cake, charcuterie, and oysters.  It’s a limited food menu but you really come for the beer in a cozy setting.  I love their signature Caramelized Chocolate Churro beer!


If you’re up for exploring other brewpubs in Chicago’s Pilsen neighborhood, check out these other two fabulous spots.


If you only have 48 hours in Chicago alone (or with friends), you cannot choose a better place for lunch or dinner than The Purple Pig.  Chef Jimmy Bannos, Jr. is a James Beard Foundation award winner and his Mediterranean wine bar has some of the best food you’ll eat in Chicago.  Also, this hot spot on Michigan Avenue is super cozy so you’ll have no problems chatting with the people sitting next to you about Chicago and the fabulous food here.



The Purple Pig 48 hours in Chicago alone 


PRO TIP:  The Purple Pig does not take reservations.  The best times to score a table or a seat at the bar without a long wait is at the beginning or end of lunchtime or late night.


If you need more inspiration for visiting The Purple Pig, check out my article on Feeding Off The Rails (my other blog) for more juicy details.


No trip to Chicago would be complete with a stop at Buddy Guy’s Legends to hear some fantastic blues.  Enjoy live blues every night and two floors filled with memorabilia including Buddy Guy’s guitars and awards, as well as the memorabilia from other legendary blues and rock artists.




Buddy Guy in Chicago 48 hours in Chicago alone



Read more about the fun times I’ve had at Buddy Guy’s Legends during Buddy’s 80th birthday bash.


PRO TIP:  Buddy Guy is in residence at his club the entire month of January from Thursday – Sunday with a different guest musician each of those nights.  So head over to the club’s website and reserve your tickets before they are sold out!


Day 2


Next, for your 48 hours in Chicago alone, start your day off with coffee or tea at Pickwick Alley.  It’s a tiny, off-the-beaten-path coffee shop in The Loop which used to be the sight of a horse stable during the Great Chicago Fire.  It is the smallest structure in Chicago’s Loop so you can take your beverage to-go or grab a table in the alley if the weather is not too cold.



Pickwick Alley 48 hours in Chicago alone

Blink at you’ll miss this hidden coffee shop located down an alley in Chicago’s Loop



Once you’ve had your caffeine fix, stroll down Michigan Avenue to the newly restored and historic Chicago Athletic Association Hotel which is located directly across from Millennium Park.  This place used to be a men’s-only club years ago.  Now, this Italian gothic-style hotel is one of Chicago’s hot spots with plenty of attractions including restaurants, bars, and a spectacular game room.  Chicago Athletic Association has one of the best views from Cindy’s Rooftop overlooking Millennium Park.  You can also enjoy the Cherry Circle Room, Milk Room the Drawing Room and Shake Shack.  



Chicago Athletic Hotel Drawing Room 48 hours in Chicago alone

Love the cozy fireplaces here!



Later on, walk off your lunch along the Magnificent Mile and head up to Tilt 360 at the top of the Hancock Tower.  This will blow your mind!  Enjoy the sweeping views of the Chicago skyline and Lake Michigan as you tilt out and away from the Hancock Building.  You’ll feel as if you literally have a bird’s eye view of The Windy City from 94 stories in the air!




Tilt 360 Chicago 48 hours in Chicago alone

Photo credit: Tilt 360 Chicago



In the evening, head up to Lincoln Park and grab some barbecue and beer at the popular Sheffield’s Beer and Wine Garden.  This neighborhood stalwart has been popular with locals for years.  The food and beer menus are excellent and the craft beers rotate daily.  If you are visiting Chicago in the warmer months, go sit in the beer garden out back.  If you’re lucky, there will be a band playing.



Sheffield's 48 hours in Chicago alone



Next up, since you are already dining in Lincoln Park, walk over to the world famous Kingston Mines for more down-home Chicago blues.  This place has two bands on its two stages 365 days a year!  Stay here and get your groove on until they turned up the lights!



Kingston Mines 48 hours in Chicago alone

Photo credit: Kingston Mines



Check my article about the 21 Awesome Chicago Music Venues for more suggestions about how to enjoy Chicago’s music scene.


I hope these suggestions for food and fun provide you with entertainment you during your 48 hours in Chicago alone!  Check back here at the blog for more additions to this series.