Weekend Getaway: Chicago

March 4, 2019 Jeffrey Olinghouse

One of the wonderful benefits to living in the US is the opportunity to visit so many diverse cities, even if for only a weekend. Whatever your style or flavor, you can reach any major US city within a few hours flight time and enjoy a couple of days of fun and relaxation. From fine dining and entertainment to culture and outdoor adventure, a weekend getaway can be an exciting investment in your marriage, mental health, or family time.

Since I live in the Midwest, I’ve discovered that Chicago is one of the easiest places to travel for a few days of downtime. In addition to its captivating skyscrapers, Chicago is home to a myriad of amenities including a host of fine dining restaurants, cultural festivals and neighborhoods, concerts, and performances. If a quick weekend getaway is the cure you seek, then Chicago is your ticket.

Here are three tips on making the most out of your weekend in the Windy City:

MEET AN OUT-OF-TOWN FRIEND

Thanks to its convenient location in the middle of the country, Chicago O’Hare airport is connected to almost every major city in the US. In just a matter of 3 hours or less, most Americans can reach Chicago by lunchtime. This direct non-stop route makes meeting friends and colleagues from around the country a breeze! In fact, if you’re planning a reunion with friends from all corners of the US, Chicago is by far the easiest, most accessible center. (Recently, my wife and I met a Madison-based friend in Chicago for the weekend. We flew directly from Tulsa, while our friend drove in across the state line from Wisconsin. Travel time for all of us clocked under 2 hours!)

In addition to the easy commute, Chicago offers an array of activities for the discerning traveler. I recommend visiting the Field Museum for natural history artifacts, cruising down Lake Michigan on a local river boat, or attending a free afternoon concert at the Chicago Cultural Center. And of course, the city boasts a full-service dining scene, ranging from casual deep-dish pizzerias and hip brunch cafes to fine-dining steakhouses. Whether you’re here flying solo or teaming up with friends and family, your schedule is sure to stay full during the weekend. (See below for links to discounted tickets for Chicago tours and attractions!)

UBER IT!

While Chicago is easily walkable, it is still a major city with a wide-spread net of restaurants and attractions. When your feet are ready for a break, just call for an Uber. We found this car-sharing service is in ample supply in the city, and it is by far the best way to get around.

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PLAN FOR ALL KINDS OF WEATHER

Chicago isn’t known for its predictable weather—in fact, its winter season and blustery winds can be quite brutal. So if you’re traveling to the city for a few days, come prepared with both indoor and outdoor plans. You’ll find your weekend progressing much more smoothly if you’re ready for sun, wind, cold, and rain!

With all that Chicago has to offer in any type of weather, you’re sure to find this welcoming city suitable to your tastes, regardless of your particular palette. Convenient and friendly, Chicago is an ideal place for your weekend destination!

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