The perfect Chicago weekend itinerary (by a local)

If you’re looking for the best things to do in Chicago on a weekend, you’re in the right place.

As a local, I love sharing all my favorite places to see in Chicago. This guide will show you how to spend the ultimate weekend, Friday evening to Sunday afternoon, in the city I call home.

From rooftop drinks with a view on Friday night to weekend brunch, shopping, strolling, dining, sipping and even beach life – this is how I would spend a weekend in the place Carl Sandberg’s poem affectionately calls the City of Big Shoulders. 

Top things to do in Chicago on a weekend

As a Chicago local (hey I’m Nausheen), these are my personal favorite things to do in Chicago on a weekend, along with my top local travel tips. But we are all different, right?

So while this is my suggested itinerary, you’ll also find plenty of attractions you can choose as alternatives to swap out for any of these recommendations, listed at the end. 

Day 1 Friday 

Rooftop dining and drinks

Kick off your weekend the right way by grabbing a drink at Cindy’s Rooftop. This stylish venue within the Chicago Athletic Association Hotel offers sweeping views over Millennium Park.

If you’re hungry, you can also order food here based on fresh, seasonal produce. However, you may want to look into making reservations in advance if you do hope to eat here as well.

Without fail, Cindy’s is where I always take guests who visit me from out of town. The cocktail menu is great, and the ideal setup is to take your drinks out to the balcony. You may have to wait a bit to get past the crowd for the best views, but it’s well worth it.

Another rooftop option I love is the J. Parker, atop Hotel Lincoln, in Lincoln Park. You’ll get great panoramic skyline views as you enjoy drinks and a full-on meal. 

Day 2 Saturday

Browse Green City Market

Between April and November, Green City Market in Lincoln Park is open on Saturday mornings between 7:00 am and 1:00 pm. This popular farmer’s market is all about supporting the community and local farmers while offering shoppers access to really good food. 

It’s the perfect place to get a coffee or shop for a picnic, which you can later enjoy at one of Chicago’s leafy city parks or at the beach! 

Brunch in Lakeview

Next, head to the Lakeview East area for brunch. This is where I used to live and it isn’t too far from Lincoln Park. You can either take an Uber, rent a Divvy city bike or even take a long walk to make your way over. 

A great spot for brunch is Wake ‘n Bacon, a super cute café serving comfort food like fried chicken on bubble waffles, grilled cheese and tater tots. And don’t forget to look up, the space is decorated with beautiful flower installations on the ceiling.

Another cool place to check out is the 2d restaurant, serving colorful Mochi donuts, juicy fried chicken and homemade lemonade fizz.

Chicago Beaches

On a nice day, spend some time at one of the city beaches. If you want to stay in Lakeview East, head to Fullerton Beach. Or, start making your way toward downtown.

North Avenue Beach is perhaps the most popular option, you can see why in the photo below! 

Oak Street Beach is another one of Chicago’s gems, close to the Streeterville and Gold Coast neighborhoods. There’s a broad stretch of golden sand, paths for walking, cycling and skating, rental concessions for bikes, beach chairs, and volleyballs. Plus, you get a beach setting with skyline views directly behind it!

If you prefer to stay active, head to the Chicago Lakefront Trail instead. It stretches for 18.5 miles along Lake Michigan’s western shore. It’s great for a long walk, run, bike or skate.

Chicago Riverwalk

Continue on closer to downtown in the River North neighborhood. Stroll along the Chicago Riverwalk to enjoy beautiful architecture, public art, drinking and dining venues in the coves, live music and more. 

After dark, between May and December, you can also see a huge digital art projection called Art on the Mart. The current mile-long Riverwalk opened in 2017 and is a fun place to be especially in the summer months.

Dinner on Randolph Street

For dinner, make your way to the West Loop neighborhood. Book reservations in advance at a fine dining restaurant on or near Randolph Street (aka Restaurant Row) for a special Saturday night out in Chicago.

Monteverde, Girl and the Goat, Elske, Leña Brava, Formento’s, Alinea, Aba and more, offer a tempting smorgasbord of choices, featuring cuisine from all over the globe.

New restaurants are constantly cropping up, and many of the best ones are concentrated in this area so do your research to choose the one that most speaks to you! 

🚁 Want to make your weekend in Chicago even more special? The best thing you can do in Chicago is to take a private Skyline Helicopter Tour. Ideal for those special occasions, this tour accommodates up to three people. It is so much fun and an experience you will remember forever!

Day 3 Sunday

The 606 

After all that rich food the night before, get re-energized by following this 2.7-mile (4.3 km) trail in Wicker Park. The elevated trail used to be a train line, and now offers lookout points, art installations, and, of course, lots of green space. Very similar to New York’s High Line Park. 

It’s the perfect area to get some cute shots to go with these Chicago Instagram captions.

Brunch at Mindy’s 

While you’re in the Wicker Park area, drop into Mindy’s Bakery for brunch. The food and pastries here are great, but the real star is Mindy’s hot chocolate with fluffy, homemade marshmallows!

Alternatively, if you’re ready to skip breakfast and go straight to lunch, Piece is a must. This spot is a local favorite known for its great pizza and buzzing energy.

Architecture river cruise 

Even as a local, I will never get tired of the Chicago architecture river cruise. It’s the perfect way to see and truly appreciate the city’s structures and skyline. 

Look out for the Willis Tower, or as locals still call it, the Sears Tower, one of the city’s best-known icons. Or if you’d rather marvel at the architecture from above, you can check out the Skydeck.

You could also drop into the Chicago Architecture Center before or afterward, which showcases the Second City’s architectural history and role in the development of the modern skyscraper. 

🌟 Click here to check price & availability >> Shoreline Sightseeing River Cruise

Best area to stay in Chicago for a weekend

If you’re only spending a weekend in Chicago, then it’s best to base yourself somewhere central. The Loop, enclosed by the “L” train tracks, is the city’s cultural hub and is packed with shops, restaurants, and bars, as well as cutting-edge museums. 

🌟 Note from Charlotte: One of my favorite hotels Downtown is the Pendry Chicago Hotel which pays homage to the gilded Art Deco era. Its location on Michigan Avenue, close to the river, means you are within walking distance of most major attractions in the city.

There are plenty of hotels outside downtown Chicago, too, which can be more affordable and peaceful places to stay.

Other great areas to stay in Chicago, close to the Loop, are Gold Coast, River North, and Streeterville. If you like to stay in a spot with a neighborhood vibe, I recommend trying Lincoln Park, Wicker Park, Old Town, or the West Loop. The latter is Chicago foodie and street art central.

Best time to visit Chicago

For first-timers in particular, I always say to head to Chicago in the summer. It becomes painfully, bone-chillingly cold here in winter months.

The city offers lots to do outdoors, including Lake Michigan and its p parks and beaches, and you can make the most of al fresco living in summer. 

Late spring or early fall can also be good, especially if you like to avoid the crowds. Accommodation prices are often cheaper than in summer, too, and you may have more options. 

How to get around during your weekend in Chicago

You can explore a lot of the city on foot, or even on two wheels. If you’re tired of walking or want to venture further afield, you can get around Chicago by using the public transport system.

The iconic “L” elevated train network is, for me, the best way to get around the city. It’s quick, efficient, and affordable. There are stops throughout the city, and services to and from both airports. O’Hare is serviced by the Blue Line.

Alternatively, use Uber, Lyft or cabs. Though rides in a car or with Lyft or Uber might cost more, it is easier than driving yourself. It can also work out cheaper, once you factor in parking fees and the car rental cost. Parking downtown can be both expensive and hard to find. 

Additional things to do in Chicago

Just in case my Chicago weekend itinerary isn’t exactly to your liking, here are a few other highlights the city has to offer.

Bike Tours

Take to two wheels to see the city from a unique perspective, there are plenty of Chicago bike tours to choose from. It is a great way to experience the city for first-timers.

Try Deep Dish Pizza

You cannot come to Chicago without sampling some deep-dish pizza! Pizzeria Uno in River North claims it’s where the dish originated.

Or write on the walls at Gino’s East on Superior; try the signature caramelized, cheesy crust at Pequod’s in Lincoln Park; ship some home from Lou Malnati’s; or break the local rules by ordering thin crust at Pizano’s. 

My all-time favorite, though, is spinach stuffed from Giordano’s, which always serves generously-sized slices!  

Chicago Greeter Tours

Take a tour of a Chicago neighborhood led by a local. Chicago Greeter Tours are completely free of charge, as they’re led by volunteers. 

Millennium Park 

You could spend hours exploring the Millenium Park Campus. As well as green space and peaceful gardens in the heart of the city, the campus is home to the McCormick Plaza for outdoor dining, the Crown Fountain, the Pritzker Pavilion for live music and movie screenings, and of course The Bean, aka Cloud Gate. This big, shiny structure appears seamless and reflects the city skyline. 

Nearby, Maggie Daley Park is a locals’ favorite, offering skating, rock climbing, tennis and mini golf. 

Museums, Galleries and Attractions

Culture vultures and artsy types won’t want to miss venues like the Museum of Science & Industry, the Field Museum of Natural History, the Chicago Cultural Center, and the Art Institute of Chicago.

Chicago attractions for those traveling with kids include the Shedd Aquarium and the Adler Planetarium. Both of these can be found at Museum Campus, a 57-acre park by Lake Michigan, along with the Field Museum. 

If nothing else, the views of the city from Museum Campus are worth taking in on their own.

Wrigley Field

For sports fans, the home of the Chicago Cubs is a must! It’s in the North Side area and surrounded by the bustling bars and restaurants of Wrigleyville.

Chicago Theater District

Enjoy a Broadway in Chicago show at one of the Loop’s heritage theaters, or even opt for Lyric Opera if you have a thing for classical music. Alternatively, the Gene Siskel Film Center is ideal for those who prefer the big screen.

Navy Pier

Navy Pier is another of the city’s most popular free attractions. The Centennial Wheel means you can’t miss it, too! As well as riding high, you can shop, dine, play, or visit museums and theaters here.

The pier, once used by the US Navy, offers sweeping panoramas of Lake Michigan. As a local, this is no longer one of my top recommendations but it can still be a fun stop to make once. 

Shopping

Want to do some shopping? Head to historic State Street. It’s home to the iconic, flagship Chicago branch of Macy’s, plus a variety of stores in Block 37.

Alternatively, pick the Magnificent Mile, the city’s retail hub. There are all sorts of stores and malls here on Michigan Avenue!

There are so many fun things to do in Chicago on a weekend that you’ll have no trouble filling up your itinerary! With its variety of distinct neighborhoods, range of restaurant options, indoor and outdoor experiences my city has SO much to offer. I can’t wait for you to discover it for yourself!

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