The late summer and early fall is a great chance to take advantage of a long weekend and squeeze in one last trip that allows you to explore all that an area has to offer, including indoor and outdoor events. For those of us in the midwest, Chicago is an excellent option for this type of trip. It’s quick and easy to get to, there’s plenty to do for everyone in the family, and of course...Chicago-style deep-dish pizza!
There’s too much to do in Chicago for us to include everything here, but we’ve listed some of our favorite activities and attractions. Additionally, for military-connected individuals, we’ll be highlighting a number of events, activities, and attractions that offer military discounts; however, we encourage you to ask about military discounts when making reservations or purchasing tickets.
Grabbing a quick flight to Chicago is simple. It’s a major American Airlines hub, so booking your flight through Contour Airlines and using the Waynesville-St. Robert Regional Airport makes everything quick and simple. Plus, any checked bags will meet you at your final destination.
Chicago’s Metra Rail connects the suburbs with downtown Chicago. It’s easy to use and relatively inexpensive, especially considering they offer a number of child, family, and military discounts depending on the time of week you’ll be traveling. The Metra Rail also allows you to stay a little farther out of downtown, yet still enjoy all the city has to offer.
Once you’re in Chicago, the Chicago Transit Authority’s (CTA) elevated trains “the L” will help you get from place to place quickly. You can view routes, schedules, and purchase tickets through their Ventra app.
Where to Stay:
As with any big city, you’ll find a wide variety of hotels to choose from. With the public transportation options, you might also consider a home sharing service, such as AirBNB or VRBO. For military travelers, we recommend looking into the Navy Lodge at Great Lakes. With free wi-fi and complimentary breakfast, as well as typical on-installation amenities, this could be an excellent option for military families.
Keep in mind that the Metra Rail connects the Great Lakes station with downtown Chicago. Once you arrive in downtown Chicago, you’ll be close to the Clinton Street station that provides access to two of the CTA’s elevated train lines.
What to Do:
This time of year provides families with an endless number of outdoor summer concerts, farmers markets, and festivals throughout the city. Whether you’re looking to immerse yourself into a specific culture, hear different types of music, or enjoy various artists, you’ll find what you want in Chicago.
Without a doubt, you won’t want to miss the Navy Pier. Originally constructed for the 1893 World Fair, kids of all ages can still enjoy rides like the swings, the carousel, and the more modern Centennial Wheel, which provides views of the entire city. Besides strolling and people watching along the pier, you can also find a funhouse maze, an indoor garden, a theater, and a children’s museum. With exceptional family-friendly restaurants and regular fireworks displays during the summer, there’s no doubt that your family could spend all day on Navy Pier and not see or experience everything.
If you have an adventurous family and want to take advantage of being outside with the great weather, consider checking out one of Chicago’s zoos: Lincoln Park or Brookfield. There are also boat or kayak tours of the Chicago waterways and bike tours that are specifically designed for kids under 10.
Chicago is also famous for its museum scene. If you have a limited amount of time, we highly recommend the Shedd Aquarium, the Field Museum (make sure to get a picture with SUE - the world’s most complete T-Rex skeleton), the Adler Planetarium, or the Chicago Museum of Science and Industry.
For military families who visit before Labor Day, the Museum of Science and Industry is part of the Blue Star Families Museums program and provides free admission for military families. We highly recommend taking advantage of this benefit, as the museum offers a wide-variety of ever-changing exhibits, including one focused on the Marvel Super Heroes (running through October 24). They also offer a giant dome theater that shows a few different movies that change from time to time.
There are four other Blue Star Museums in the downtown Chicago area. They are:
Chicago Gamespace - perfect for video game enthusiasts, though they’re only open on Sundays from 1-5 p.m.
There are an additional 10 museums in the suburbs of downtown Chicago that also participate in this program. If you choose to stay outside downtown, make sure to check out the Blue Star Families website and look for a museum that might be close to where you’re staying.
Regardless of where you stay and what you choose to do while you’re in the city, Chicago is a great choice for families. Enjoy your planning and the many memories you’ll make during your visit!