How to Do Chicago Right (on a Weeknight)

July 28th, 2022
Chicago skyline

When attending the LEND360 conference in Chicago this September, you may be looking for interesting ways to spend your evening hours. To help you find the perfect Chicago experience, we compiled this list of things to do on a weeknight in the Windy City.


restaurant in Chicago, IL

If you’re looking for a great place to eat in downtown Chicago, you won’t be disappointed. There are so many excellent restaurants to choose from, whether you’re looking for a casual meal or a fine dining experience.

One of our favorite eateries include Alinea, which is one of the most acclaimed restaurants in the city.

For something a bit more casual, try Publican Quality Breads for some of the best sandwiches in town.


bar in Chicago, IL


If you’re looking to relax after traveling, there are many great bars in downtown Chicago.

One of the best is Three Dots and a Dash, which is a tiki-themed bar with an extensive list of rum-based cocktails. If you’re looking for something different, be sure to check out this spot.

theater in Chicago, IL


Looking for a great way to spend your evening in downtown Chicago? Check out one of these top-rated theaters!

The Chicago Theater: This historic theater has been entertaining audiences since 1921 and continues to be a popular destination for both locals and visitors. With a wide variety of shows on offer, there’s something for everyone at The Chicago Theater.

The Goodman Theatre: Another long-running theater in Chicago, The Goodman has been putting on world-class productions since 1925. From dramas to comedies and everything in between, this is the place to go if you want to see the best of what Chicago theater has to offer.

The Steppenwolf Theatre Company: One of the most acclaimed theater companies in the country, Steppenwolf is renowned for its cutting-edge productions. If you’re looking for an evening of thought-provoking entertainment, this is the place to be.


We’ll leave it up to you to decide just how exciting you want your weeknight to be – but if you’re looking for a great night out on the town, then you’ll want to check out some of the best nightclubs in the area.

The Underground is one of the most popular clubs in the city. This club is known for its amazing music and incredible atmosphere. If you’re looking to dance the night away, then The Underground is the place for you.

If you’re more into hip hop, then you’ll want to check out Sound-Bar. This club is known for its incredible sound system and its amazing lineup of DJs and boasting some of the best hip hop music in the city.

Finally, if you’re looking for a more laid-back atmosphere, then you’ll want to check out Easy Bar. This bar is known for its great drinks and an eclectic jukebox – dancing optional.

biking in Chicago, IL

Getting Around Downtown Chicago

If you’re staying in downtown Chicago, take advantage of the city’s excellent public transportation system and leave your car at your hotel. The ‘L’ train can get you around to all of the popular destinations in downtown, and you can even purchase a day pass if you plan on doing a lot of sightseeing.

If you prefer to walk, many of the attractions and restaurants are located within convenient walking distance of each other.

If you’re looking for something more active, rented bicycles are widely available in the city.

chicago bean

If You’re Visiting Chicago For The First Time…

If you’re visiting Chicago for the first time, there are plenty of things to do in the evening, we have a few must-see recommendations for your visit.

First, check out one of the city’s many iconic landmarks, such as the Willis Tower or the Cloud Gate sculpture in Millennium Park.

Then, explore some of Chicago’s diverse cultural neighborhoods, such as Wicker Park or Chinatown.

Finally, sample some of the best food and drink that the city has to offer, from signature deep dish pizza to local craft beer.


As you can see, Chicago has a lot to offer visitors. We can’t wait to experience it all! Valmar Merchant Services and Totality will be at LEND360 this September, so if you decide to check out some of these recommendations, be sure to stop by our booth and tell us all about your travels.

We’ll see you on The Magnificent Mile!

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