Chicago offers a full agenda for any weekend visit. To narrow down the options for a perfect trip, we’ve partnered with family traveler (and Chicago resident) Kirsten Maxwell from Kids Are A Trip. She shares some favorite things to do and places to eat to have the perfect Chicago weekend.

Chicago is a city that attracts visitors year round with its stunning architecture, stellar food scene, and beautiful Lake Michigan views. Tourists want to visit all the top attractions and sample the deep dish pizza. That’s a great plan, but here’s a few new ideas for how to have the perfect weekend in Chicago.

Day 1: Getting Settled

Most visitors will arrive at one of Chicago’s two airports, Midway or O’Hare. Both can be anywhere from thirty minutes to an hour drive from downtown depending on the time of day. Taxis and public transportation are readily available at both.

Head downtown and check into one of the centrally located hotels along or just off Michigan Avenue (also known as the Magnificent Mile), such as Loews Chicago or The Chicago Athletic Association Hotel. Both properties have spectacular rooftop restaurants and bars for views of the city and central locations.

Once settled, head to one of the tallest buildings in the city, The Willis Tower or 360 Chicago (formerly John Hancock Observatory). At Willis Tower, take an elevator to the 103rd floor and experience “The Ledge” where visitors walk out on a glass platform 1,353 feet above the streets below. Another opportunity to be daring is “Tilt” at 360 Chicago where people step onto a glass platform that “tilts” away from the building and suspends them 1,000 feet above Michigan Avenue. If these aren’t your speed, simply enjoy the views of the city from above before heading back to street level.

Before dinner, grab a cocktail from a rooftop bar and enjoy the sunset view. Many hotels allow non-guests to have access to their rooftops. If you would rather skip the cocktails and head straight to dinner, consider one of these top choices. The Purple Pig right off Michigan Avenue and the Chicago River serves creative and delicious small plates in a family style setting. Eataly is another option for a unique Chicago experience. The 63,000 square foot building houses aisle after aisle of groceries and 22 plus restaurants and bars. Options vary from pasta and pizza to a Nutella bar. Those looking for something more formal should head to RPM Italian or RPM Steak. It’s impossible to go wrong with either one.

Day 2: Get Out and Explore

Wake up early and head to Michigan Avenue or the Chicago River for a walk before the crowds arrive. Grab a bite to eat at Wildberry across from Millennium Park or Yolk (multiple locations). Both offer extensive breakfast menus with hearty meals that will keep you going all morning long.

Afterwards take your car or hop on the train to the Chicago suburb of Naperville. This city is the perfect combination of restaurants, attractions, and entertainment. Here is where you will find one of Chicago’s Topgolf locations, where families of all ages and abilities can make a day of driving golf balls from their own hitting bay and playing games of distance and accuracy. Think of TopGolf like a bowling alley for golf, but better. Families have their own comfortable couches and a server that brings them food and beverages while they’re enjoying their games.

Topgolf isn’t just about golf, there’s also interactive video games, giant Jenga, pool tables, music, and more. They also have a creative chef-driven menu with fun adult cocktails and a menu just for the kids. When you’re done playing and eating lunch, head over to the Naperville Riverwalk. Take a stroll and enjoy the fountains, sculptures, and bridges before returning to the city for the evening.

Photo: Michael Baxter, Baxter Imaging LLC

If you still have some energy left, consider going to the theatre. Popular shows include Blue Man Group and The Second City improv comedy show. Broadway tickets may be available for performances at the Ford Oriental Theatre, Cadillac Palace Theatre, or PrivateBank Theatre. A good site to use for last minute tickets is TodayTix.

Popular dinner spots for a pre-show meal include Petterino’s (old school Italian restaurant), Atwood (American bistro), and Latinicty (a delicious up-scale Latin themed food court).

Day 3: Take it Easy

Assuming it was a late night, today’s a great morning for donuts and Chicago has plenty of them. Some favorites include: Doughnut Vault (go early before they sell out), Firecakes, Do-Rite, and Glazed & Confused. There are no bad choices at any of these shops.


Chicagoans are quite obsessed with donuts! Photo: Kids Are A Trip

If brunch is more your speed, consider heading to Beatrix, The Publican, or Summer House Santa Monica. Be sure to bring your appetite.

If the weather is great, head to Millennium Park early and admire the Cloud Gate sculpture (aka “The Bean”), Crown Fountain, and Lurie Garden. Walk over to Maggie Daley Park and admire the massive playground and climbing wall. In the winter, there’s a skating ribbon that winds its way through the park. It’s amazing to stand on a high point and see Lake Michigan to the east and the city skyscrapers to the west.

Consider spending a few hours or the rest of the day at Chicago’s top museums. There are many options in the downtown area. The Art Institute is Chicago’s premiere art museum that has been named the best in the world. Shedd Aquarium features dolphins, penguins, and other marine life. The Field Museum is dinosaurs and mummies and everything in between. Adler Planetarium offers an up close view of our universe. The Museum of Science and Industry offers hands-on exploration of everything from submarines to farm equipment. Consider purchasing a CityPASS if you want to see more than one attraction.

It wouldn’t be a visit to the Windy City without some deep dish pizza, so I’ll leave you with a couple of recommendations. Giordano’s and Lou Malnati’s usually claim they are “the best”, but other delicious options include Pizzeria UNO and Pequod’s Pizza. After you’ve had a chance to try any of them, you’ll be counting the days until your next visit.

Kirsten Maxwell is an official Travelocity Gnational Gnomad. Gnational Gnomads is an exclusive group of high-profile travel and lifestyle experts who offer tips and inspiration on behalf of Travelocity. For more information on the Travelocity Gnomads, visit

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

Pin It on Pinterest

Share This