How to Spend a Summer Weekend in Chicago

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It’s the most wonderful time of the year: summer in Chicago.

Last June, I had the pleasure of planning a mystery trip for a couple of travelers to my home city: Chicago. I may be biased, but I think there are few better places to spend the summer than the Windy City. Everyone has come out of hibernation, patios and rooftops are open for business, Lake Michigan is sparkling and inviting, there’s a ton to do, and the whole city has a vibrancy that you can feel. With that in mind, here are a few tips for how to spend a weekend in Chicago during its best season.

Be outside as much as possible.
Look, Chicago has some world-class museums, but if you want my advice, save these for rainy or colder days and take advantage of the beautiful weather. There is no shortage of things to do, but here are my favorites:

  • Take long walks to explore the city. Each neighborhood offers something different, so slip on some comfortable sandals and head out on an adventure. While downtown, try strolling the Riverwalk, which runs along the south bank of the Chicago River between Franklin Street and Lake Shore Drive, and stop for a drink or a snack at one of the many little cafés along the way. You might also try taking a pay-what-you-want walking tour with Free Tours by Foot.
  • Take a boat cruise with the Chicago Architectural Foundation. Chicago’s architecture is known worldwide, and this 90-minute river tour gives you a chance to learn about more than 50 buildings and the history of how Chicago grew from a small outpost into one of the world’s largest cities in less than 100 years.
  • DeniseKatie - Cubs gameGo to a Cubs game. If they’re playing out of town, you can still take a tour of the historic ballpark. (I’m a North Sider, so I root for the Cubs, but you can also head south to U.S. Cellular Field to catch a White Sox game.)
  • Get out on beautiful Lake Michigan. You can rent a boat, take a sunset sail, go kayaking, bike along the 18-mile lakefront path, or simply spend some time at one of the beaches.
  • 20140807_205625Catch a free concert in Millennium Park. Grab some picnic food (bottles of wine and other adult beverages are A-OK) from one of the many restaurants near Michigan Avenue and head to Pritzker Pavilion for one of their 6:30 p.m. free symphony concerts.
  • Spend some time on a bar or restaurant patio. A few favorites are Big Star (tacos and margaritas), Parson’s Chicken and Fish (order a Negroni slushy), and Pub Royale (draft beers and ciders, cocktails, and Indian pub fare).

Then head indoors for this can’t-miss, quintessential Chicago activity.
When you’re in Chicago, you must take in a show at The Second City, the city’s legendary improv comedy club, where many greats got their start: Chris Farley, Dan Akroyd, Jim Belushi, Steve Carell, Stephen Colbert, Tina Fey, Amy Poehler, and many more. You can take your pick between the shows at the Mainstage or the E.T.C. stage, but book ahead because many shows sell out.

Prepare to eat and drink well.
Chicago’s food scene is so much more than hot dogs and pizza, so make sure you carve out some time for great meals. Here’s what Bon Appétit has to say:

“The Windy City has always been one of our favorite eating destinations. With its mix of confident cooking, brazen portions, diverse inspirations, and great local ingredients (not to mention the fact that everyone is so friendly—and so into food), it’s where you go for a big, fat weekend, or tack on an extra day to your business trip to squeeze in a few more reservations. (Did we mention the drink’s top-notch, too?) Definitely our kind of town.”

There isn’t possibly time to list all the great restaurants you could visit, but here are some of my favorites:

  • Lou Malnati’s—This is the gold standard in Chicago deep-dish, with the recipe passed down for decades from essentially the Godfather of Chicago Pizza.
  • Bavette’s Bar and Boeuf—Chicago has a lot of great steakhouses, but this newer French-style one, with its 1920s-style ambience, is the one I always want to come back to. You don’t even have to order steak; all the food is delicious, the cocktails are excellent, and please order the chocolate cream pie for dessert.20150902_225132
  • Au Cheval—This trendy, upscale diner serves quite possibly the best burger you’ll ever have. It doesn’t take reservations, so be prepared for a wait, but luckily it’s located on Randolph Street’s Restaurant Row, so you can wander the neighborhood and grab a snack or a drink at one of the many other hotspots while you’re waiting for your table.
  • Little Goat Diner—If you’re a Top Chef fan, you may remember Season 4 winner Stephanie Izard; this is one of her restaurants. Her empire also includes Girl & the Goat (innovative small plates) and Duck Duck Goat (creative Chinese cuisine), both of which require reservations far in advance. Little Goat is a fun, no-reservations spot where you can try her delicious food (think imagine American favorites).
  • Frontera Grill—In addition to pizza and street food like hot dogs and Italian beef, Chicago has a reputation for fantastic regional Mexican cuisine, thanks to the large segment of the city’s population with Mexican heritage. This spot, which serves creative, yet authentic Mexican dishes, is helmed by noted chef Rick Bayless, who has spent lots of time traveling, learning, and cooking in Mexico. A limited number of reservations are taken, but most tables are for walk-ins. If you aren’t seated right away, just try one of the fantastic margaritas while you wait!

Travelers, this just scratches the surface of all there is to do (and eat) in this great city. I could go on forever. But instead, come visit and see for yourself—or have Magical Mystery Tours plan a trip for you!

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