Eating Chicago in 2 Days (Vol. 3)

Welcome to the third installment of my Eating Chicago in 2 Days blog series!  I understand that it can be overwhelming trying to navigate a huge food destination like Chicago especially when you only have a couple days to spare.  That said, I have put together a few two-day food itineraries to help take the guesswork out of where to find the best food and drink around town.  Climb aboard and let’s go Feeding Off The Rails!


Day 1 – Eating Chicago in 2 Days (Vol. 3)



The Midwest is known for having hearty baked goods and there are a number of Sensational Chicago Bakeries that will make you drool.  Baker Miller is high on that list.  Start your first day of eating Chicago in two days at this homey Lincoln Square bakery.  All the baked goods are terrific and I have a soft spot for

their homemade oatmeal.  Make sure to mix in some of the fabulous jams while you’re dressing up your bowl.




Chicago Bakeries Baker Miller Lincoln Square Eating Chicago in 2 Days

Homemade oatmeal with cultured cream, milk, pecans, and jam. Sooo comforting!


4610 N. Western Ave. – Take the Brown Line to the Western ‘L’ stop.




Any trip to Chicago should include a meal or cocktails overlooking the Chicago River with its view of the stunning skyline and iconic bridges.  When it’s time for lunch, head to The Kitchen in River North.  Here you will enjoy a great view of the city as well as a creative menu.  Sit at the bar or a table and enjoy the great entrees and desserts.  If you’re into decadent seafood towers, they have them, too.




Walleye at The Kitchen Chicago in 2 Days



316 N. Clark St. – Take the Green, Blue, Pink, Purple, Orange and Brown Lines to the Clark/Lake ‘L’ stop.




In the evening, wander south to Chinatown and check out Strings Ramen.  This small but cozy spot leads the list of Chicago’s Best Ramen Shops.  The noodles are hand-pulled and the broths are deep and complex.  There is more than just noodles on the menu here (e.g. sashimi) and it’s BYOB.  




Strings Ramen Shop in Chicago Eating Chicago in 2 Days


2141 S. Archer Ave. – Take the Red Line to the Cermak-Chinatown ‘L’ stop.



Chicago has a vibrant nightlife and when you’re trying to get the most out of Chicago in 2 days Cindy’s Rooftop should be on your list.  If you haven’t heard, Cindy’s is the popular new restaurant/bar inside the newly restored Chicago Athletic Association Hotel on Michigan Avenue.  It’s one of a few places inside the hotel to enjoy a cocktail but it is the only one with a terrace that overlooks Millennium Park and Lake Michigan.  Order a cocktail and head out onto the terrace near one of the firepits.  In the summer, this is one of the best spots to watch the fireworks on Wednesdays and Saturdays.




Chicago bars Cindy's Rooftop in Chicago Eating Chicago in 2 Days

Cindy’s Rooftop is one of the hottest dining destinations in Chicago.




Cindy's Rooftop Terrace Chicago in 2 Days

View looking at The Adler Planetarium from Cindy’s Rooftop Terrace



12 S. Michigan Avenue – Take the Green, Orange, Brown Pink and Purple Lines to the Washington/Wabash ‘L’ stop.


Day 2 – Eating Chicago in 2 Days (Vol. 3)



On your second day in Chicago, get buzzed on coffee and the hustle and bustle of The Loop at Dollop.  This busy coffee shop is located in the heart of downtown underneath the ‘L’ tracks near Harold Washington Library.  It is an essential stop for the work crowd but I like to bring my laptop and work while watching the city move around me.  Dollop is one of Chicago’s 30 Coolest Coffee Spots




Chicago in 2 Days Dollop coffee

Dollop coffee shop in The Loop


343 S. Dearborn St. –  Take the Brown, Orange, Pink and Purple Lines to the Harold Washington Library (State/Van Buren) ‘L’ stop.




By now, you’ve learned from this blog that Chicago is very accessible via mass transit.  Do not spend all of your time in The Loop or near downtown.  Instead, go explore the food scene in Humboldt Park on the west side.  I love this gritty neighborhood with its beautiful boathouse, restaurants, and bars.  Cafe Marie-Jeanne is one of the prettiest and peaceful places to enjoy a meal or three throughout the day.j  It made my list of Best Restaurants of 2017.  Avoid crowds at Cafe Marie-Jeanne by coming for lunch.  The food has a French twist and the smoked fish and meats are divine.  If you don’t have to work, try one of the beautiful cocktails or wine.




Romantic Chicago Restaurants Cafe Marie Jeanne Chicago Eating Chicago in 2 Days



1001 N. California Ave. – Take the Blue Line to California ‘L’ stop and transfer to the #52 Kedzie/California bus south to Augusta Blvd.




After you’ve enjoyed a leisurely lunch at Cafe Marie-Jeanne, walk across the street to Spinning J, an old-fashioned bakery and soda fountain.  While Spinning J serves a lunch menu, you should really order one of the homemade ice cream sodas or pies.  This place gives me the warm and fuzzies!




Chicago Bakeries Chicago Dining Roundup Spinning J Chicago Humboldt Park Chicago in 2 Days

Ginger-lime soda with blackberry-lime gelato float



1000 N. California Ave. – Take the Blue Line to California ‘L’ stop and transfer to the #52 Kedzie/California bus to Augusta Blvd.




Round off your experience of eating Chicago in 2 days by making a dinner reservation at Giant in Logan Square.  This place is one of the current darlings of the Chicago food scene and the praise is well-deserved.  I stopped by one night and enjoyed a smokey, spicey swordfish dish and a very creative squash plate.  The menu at Giant is always changing and the chef always brings his “A game.”  




Chicago in 2 Days Best Logan Square Restaurants Best restaurants of 2016 Chicago Dining Roundup Swordfish Giant Chicago

Oh, this swordfish!


3209 W. Armitage Ave. – Take the Blue Line to the Western ‘L’ stop and transfer to the #73 Armitage bus going west.




When you’re finished with dinner at Giant, walk next door to Scofflaw for some drinks to say farewell to Chicago.  This Victorian-style bar has amazing cocktails, many with a gin focus.  Scofflaw is one of the many great bars in Chicago you must visit.




Chicago in 2 Days Scofflaw Logan Square



3201 W. Armitage Ave. – Take the Blue Line to the Western ‘L’ stop and transfer to the #73 Armitage bus west.



If you missed my first installment of Eating Chicago in 2 Days – Vol. 1, check it out.


In keeping with the spirit of Feeding Off The Rails, I encourage you to leave your car at home and ride the CTA trains and buses as you begin Eating Chicago in 2 Days.  Save on gas. Avoid traffic, road rage and parking.  Reduce pollution. Don’t drink and drive!