Updated. Originally posted on June 13, 2019.
Chicago is a great weekend destination. It is big enough to be a global city, but small enough for exploration. World-class museums, renowned architectural buildings, Michelin-star restaurants, diverse neighborhoods, and a legendary musical haven – there’s more than enough reason for everyone.
But the secret to spending a great weekend getaway is knowing your priorities. Sometimes, too many options can be a bad thing so make sure you have an idea of how you would like to spend your time.
Spending a weekend in Chicago for the first time can be overwhelming. Or in any big city really. So I whipped up a helpful guide that can serve as your starting point.
Friday Night
A great city comes with a great night life. Chicagoans are workers. But they are also drinkers. When the clock hits five o’clock on a Friday, the bars and restaurants fill up so make a reservation ahead of time.
Where to go:
- The Signature Lounge at the 96th Floor – Grab drinks 1000 feet high with the best view of Chicago. Drinks are pretty expensive but you are paying for the view and experience. You can also catch the most beautiful sunset if you go at the right time.
- Giordano’s – Just a few blocks from the Signature Lounge, walk to Giordano’s for dinner and experience Chicago’s famous deep-dish pizza. You must make a reservation as it gets really busy. Also, deep-dish pizza takes 45 minutes to make, so plan accordingly.
The Drifter – Only a fifteen-minute walk from Giordano’s, end the night with drinks at Chicago’s well-kept secret, The Drifter. It is a speakeasy underneath the historical Green Door Tavern, Chicago’s oldest drinking establishment. This is a very busy spot on weekends so make sure you get on their waiting list as soon as possible. The neighborhood is also full of bars and clubs if you don’t like waiting.
Did you know?
If the door of a restaurant was painted green during prohibition, it indicated the presence of a speakeasy in that establishment.
Saturday
Where to go:
- Wildberry Pancakes & Cafe – For brunch, head to this cafe located in the heart of downtown Chicago. They literally have everything for everyone. Plus, it is located right across Millennium Park which is your next destination. Very convenient.
- Millennium Park – You can’t go to Chicago without checking out its most famous landmark, The Bean, which is located within the park. The 25-acre park hosts free art installations, outdoor concerts, film screenings, outdoor workouts and tours. It remains a hot spot for travel itineraries year round.
Did you know?
The iconic structure known as “The Bean” is not its real name. Its official name is Cloud Gate.
- Magnificent Mile – The Mag Mile offers the best shopping experience in Chicago. It includes a number of art galleries, luxury boutiques, hotels, historical landmarks, theaters, restaurants, and pubs.
- Architecture Boat Tour – If you have time to spare and would like to do an activity, the architecture boat tours are the best way to enjoy the sights especially in the summer.
Saturday Night
Where to go:
- London House Rooftop Bar – For a lowkey night with killer city views, head to the London House Rooftop Bar located in London House Chicago. It offers one of the best views of the city.
You can’t spend a weekend in Chicago without experiencing its nightlife. If you want an energetic Saturday night, head to River North area where you can find establishments like Joy District, a hip restaurant & cocktail bar with a roof deck & late-night dancing, and Celeste where you have four floors of fun including a disco floor and a roof top garden lounge. For music lovers, there’s the House of Blues or Untitled Supper Club. I highly recommend the Green Mill, one of Chicago’s many historical landmarks. It is outside Downtown Chicago but it is worth it!
Sunday
Where to go:
Cabra- Chicago has a lot of famous chefs and multi-awarded restaurants. It is also a big brunch city. One of my favorites – Cabra, owned by Top Chef Stephanie Izard, is a rooftop Peruvian-inspired restaurant in Chicago’s West Loop area. It is not only a great place for brunch but for dinner as well.
Navy Pier – You can pretty much spend the rest of your day here. Navy Pier is best during summer as it becomes livelier and offers more fun things to do. It is one of Chicago’s landmarks , and a must see for any visit to Chicago. The Navy Pier is a fifty-acre playground for all locals and tourists alike, and offers theater, museums, music, restaurants, shops and the first ferris wheel’s brother — Centennial Wheel.
When in Navy Pier, don’t forget to try Chicago’s Original Rainbow Cone, a five-layered ice cream!
Did you know?
The first ferris wheel was invented in Chicago by George Washington Ferris and was unveiled at the 1893 World’s Fair in Chicago. More than 120 years later, Chicago adds to its legacy with a new Ferris wheel on Navy Pier.
To make the most of your weekend, a Chicago CityPASS is a good way to spend less and experience more. If you want to focus your precious time at the city’s iconic attractions, this is offers just that.
And for some reason you only have a day to spare instead of a weekend in Chicago, it’s still possible to squeeze in some of the top attractions!
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Jen is a Chicago-based traveler and creative. She is a full-time development & communications executive specializing in non-profit organizations. Originally from the East Coast, she created The Jetsetter as a place to share her travel stories and photos with friends and family. Now, it is a place for adventurers and dreamers. Its purpose is to inspire and encourage busy professionals to see the world and achieve a better work-life balance.
OMG, I’d go just for that ice cream cone! I’ve traveled through much of the US, but never been to Chicago. I’d love to see it someday…
Chicago should be on your list!
I’ve been thinking about taking a road trip to Chicago! This article is even more motivation to make that happen SOON!!! The view from the rooftop alone is enough to make me want to jump in my car now.
You should def visit Chicago! Summer is the best time to go!