How to Simplify Your Weekend in Chicago Itinerary


City Weekends

I’m always ready to travel. Even a weekend is enough to get a snapshot of a locale, When I get away I most often choose to try a new city.  Although I love the beach, I am naturally a city person. My idea of fun is: food, art, music, and discovering what makes a place unique. My greatest challenge is usually how to pack in so many experiences. Since I live in the Chicago area, I have lots of time to explore it. Fortunately, it’s always evolving, I never fail to discover new places and neighborhoods. Nevertheless, as a resident, I’ve also uncovered some secrets that can simplify any weekend in Chicago itinerary. Let me help you plan your trip so you can focus on having fun.

Downtown Chicago
Downtown Chicago

Weekend in Chicago Itinerary

It is easy to spend a weekend in Chicago and never leave the neighborhood near your hotel. The downtown area is packed with theater, shopping, museums, and landmarks. When I travel I want to see the famous spots, but I also try to get the local perspective. I want to see where people go when they’re not on vacation. Although you’ll see plenty of Chicagoans shopping on Michigan Avenue, or enjoying the patios of West Loop restaurants there’s a lot to be found in neighborhoods throughout the city.

Thalia Hall, part of a Chicago Weekend Itinerary
Thalia Hall

Easy Weekend in Chicago Itinerary

Even though I live here, I appreciate when a music venue or museum has a good restaurant, a coffee bar or a spot for cocktails. Fortunately, one of Chicago’s most intimate concert halls, Thalia Hall has two out of three. In addition to Thalia Hall, the building houses a gastropub, Dusek’s Board and Beer, and two bars, Punch House and Tack Room. It’s a short Uber ride away in Pilsen, a neighborhood, popular with Mexican immigrants, southwest of downtown.

Dusek's, part of a Chicago Weekend Iinerary
Dusek’s at Thalia Hall

Punch House

If I’m seeing a concert with a group I like to start the evening at Punch House. It’s in the basement below Dusek’s. Decorated like a relative’s 1970’s rec room, their specialty is punch recipes. Divided into classic and contemporary categories, you can get them by the glass, carafe or bowl.  I think my favorite punch is Space Juice for Jereda blend of tequila, citrus and sparkling wine spiced with black pepper and sage. If you like your punch with champagne, there’s tableside champagne punch service for six.

The food at Punch House is also meant for sharing. Try the fondue, shishito hushpuppies, or Dusek’s famous Sourdough Pretzel EPI.

Punch House
Punch House

Dusek’s Board and Beer

Dusek’s is a laid-back neighborhood spot that has a curated craft beer selection and amazing food. Winner of a coveted Michelin star, it’s a place where you’ll be equally happy whether you get the cheeseburger or the steak tartare. Open for brunch, lunch, dinner, and late night, the restaurant offers upscale comfort food. Since some diners are mainly here to see the music, snacks, sandwiches and a dessert menu are all available. Personally, I have to admit to an addiction to their chicken-fried rabbit. I also find the plate of artisanal hams and duck fat fries hard to resist. Others I know, are dedicated to the lamb sausage sandwich. It’s a popular place, so I recommend making a reservation.

Dinner at Dusek's
Dinner at Dusek’s

Thalia Hall

Thalia Hall is one of my favorite places to see music in Chicago. The building is a historic landmark, commissioned by tavern keeper John Dusek in 1892 as a multi-purpose community hall. At the turn of the last century, it contained commercial storefronts, residential housing, and a public hall. Modeled after a Prague opera house, John Dusek built Thalia Hall with the intent of bringing music and the arts of Bohemia to his bohemian neighbors. The ornate theatre fulfilled it’s mission, functioning both as a gathering spot and a center of entertainment in the neighborhood for over 70 years, Closed in the 60’s, the property was bought by 16 on Center hospitality collective in 2013. They launched three new concepts in the beautifully restored Thalia Hall: a  beer-inspired restaurant, a punch-focused bar, and an event space that hosts established musical acts.

Sourdough Pretzel EPI
Sourdough Pretzel EPI

Tack Room

Just because you don’t have tickets to see a favorite band at Thalia Hall doesn’t mean you can’t see live music here. The Tack Room, a cozy cocktail bar offers regular entertainment in the form of a piano bar. A patio and a small menu of snacks, sandwiches, and desserts have also contributed to it becoming a destination of its own.

Shishito Hush Puppies - weekend in Chicago itinerary
Shishito Hush Puppies

Add Art to Your Weekend in Chicago Itinerary

If you enjoy art, get to Pilsen before 5 pm and visit the free National Museum of Mexican Art. It’s a wonderful small museum. You can immerse yourself in both Mexican art and its culture here in Chicago. Don’t miss the gift shop, its a treasure trove of work from contemporary artists.

Contemporary Mexican Art from The National Museum of Mexican Art - weekend in Chicago itinerary
Contemporary Mexican Art from The National Museum of Mexican Art


I hope you enjoy Thalia Hall and the Pilsen, It’s a fun area. It adds something out of the ordinary to your weekend in Chicago Itinerary.

If you are looking for other travel ideas read my posts about Portland, OR, Portland, ME, and DC.

The Lincoln Memorial
Lincoln Memorial

Changing the name of my blog to A Chicago Life

As I mentioned in my last post, How to Discover if You are Meant to be a Food Blogger, I’m changing my blog to give readers a wider range of useful information. To reflect the addition of posts not related to food or wellness I will be changing the name of my blog to  A Chicago Life.






Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.