Joseph Hernandez a RoamRight Blog Author

Visiting Chicago with Your Family

RoamRight shares tips on visiting Chixago with Your Family
Image source: Flickr - Bryce Edwards

With its slew of activities, access to public transportation and easy-to-navigate streets, the Windy City is an ideal place to spend some time with the kids. Here are some tips for getting around.

The El

Chicago’s elevated trains are an attraction in and of themselves. When in the downtown Loop area, any of the colored lines will take you to the city’s friendly neighborhoods in short order. Got on the wrong train? Don’t fret. The El system is easier to navigate than New York’s subways, since the Loop is just that: trains loop around the city and will return to you eventually. Just hop back on!

Chicago River

During the warm months, there is no better way to experience the city than from an architectural river cruise. Chicago Line Cruises provides a 90-minute cruise on the iconic Chicago River, offering a glimpse at the city’s world-class architecture and its history as the center of vertical urban planning.


Chicago is at its absolute best in the spring and summer. Time your visits around these months and you’ll enjoy sunshine-filled days and festivals galore. The city takes its street fairs very seriously and you’ll often find three or four festivals that pique your interest on any given weekend. Highlights include the South Loop’s Printer’s Row Lit Fest, Retro on Roscoe in the family-friendly Roscoe Village, and the iconic Oktoberfest in the Lincoln Square neighborhood.

The Grid

After the Great Chicago Fire, city planners went to work implementing a modern city plan, so much of the Northside is laid out on a perfect grid. From its start at State and Madison (coordinates 0 E/W, 0 N/S, respectively), it’s easy to determine cross streets, locations and distances based on the coordinates. Each city block, in all compass directions, increases by 100, with 8 blocks being a mile, with arterial streets being found at every half-mile. Once you get acclimated to this grid, you can find your destination in short order.


Want to keep the kids busy? Check out any number of Lake Michigan-abutting attractions and you’ll be set. The Lincoln Park Zoo is free and provides hours of gawking at otter, giraffes and monkeys, while a 10 minute walk to North Avenue beach affords you an urban beachside view of Chicago’s iconic skyline. For more cultural offerings, head south to Grant Park and take in the Adler Planetarium, Field Museum and Shedd Aquarium, all conveniently located within steps of one another. Of course, Navy Pier, which houses the Chicago Children’s Museum, is the perfect place to spend the day amongst rides, food carts and in the fresh air. Don’t forget to snap the requisite family photo with the Art Institute’s iconic lions!


Chicago is one of the U.S.’s best food cities. While people have their favorite deep dish and hot dog haunts, it can be agreed that they’re all worth trying. Fill the kids up at Pequod’s Pizza in Lincoln Park. While not 100% “true” Chicago-style pizza, its deep-dish pie is just as satisfying and less messy. A true Chicago-style hot dog gets the gourmet treatment at Hot Doug’s, while at Kuma’s, you’ll find out-of-control burgers in a rock-and-roll setting. When it comes to breakfast, nothing beats Ann Sather’s famous cinnamon rolls, found at multiple locations. The best thing about Chicago’s food scene is that hole-in-the-wall ethnic bites can go toe-to-toe with its heavy-weight Michelin Star holders, which means every meal will be memorable.

Are you ready to take a family vacation to the Windy City?

Note: Available plans and coverages may have changed since this blog was published.

About the Author

Joseph Hernandez

Joseph Hernandez, a RoamRight Blog Author Raised in Southern California, Joseph left the temperate climes of the OC for the chilly winters of Chicago, where he earned his degree in magazine journalism. Along the way, he developed an impenetrable layer of blubber, thanks to the city's deep dish pizza and hot dogs. In recent years, he has edited an online travel magazine, helped produce two international TBEX conferences, and has written about fashion, food, wine, and travel for various online publications. Currently, Joseph is Assistant Editor at Wine Enthusiast Magazine, where he geeks out on his interests regularly. Read Joseph's blog at Pith + Moment or follow him on Twitter.

Get A Free Travel Insurance Quote 

Travel smarter with travel insurance from RoamRight. Get your free, no-obligation quote online today.

I'm a partner, take me to my portal

Stay Connected!

Sign up for RoamRight's FREE monthly email newsletter to get travel tips, tricks, news, ideas, and inspiration!

The RoamRight mark is used by Arch Insurance Company and owned by its parent company, Arch Capital Group (U.S.). Insurance coverages are underwritten by Arch Insurance Company, NAIC #11150, under certain policy series, including LTP 2013 and amendments thereto. Certain terms, conditions, restrictions and exclusions apply and coverages may vary in certain states. In the event of any conflict between your policy terms and coverage descriptions on this website, the terms and conditions of your policy shall govern. Click here for privacy notice.

Copyright© 2024 Arch Insurance Company. All rights reserved.