Chicago Staycation Ideas: Explore the City of Neighborhoods

July 8, 2015

This blog post first appeared, written by me! I’ve done everything on this list and can honestly say these are some of my top Chicago staycation ideas. There are so many more wonderful places to explore. Post a comment if you’re heading to Chicago and want some more recommendations!

Yea, yea, yea Millennium Park and The Bean (officially Cloud Gate) are awesome, as is shopping the Magnificent Mile, but elbowing through the summer tourist crowds is not. There are so many unique places to explore in Chicago, which is truly a city of neighborhoods. If you’re anything like me, you rarely leave the 10-mile radius of your home, and stick to your neighborhood favorites when going out. Summer is most definitely the best time to explore Chicago. If you’re longing for a vacation or weekend getaway, but don’t have the time or money – Give a Chicago staycation a try!

Explore Logan Square: If you consider yourself “creative,” love guys in plaid shirts with beards, and are into the food scene – try Logan Square. For the ultimate staycation experience, book at night or two at Longman & Eagle, not only is this top restaurant and whiskey bar a great spot for a meal, but also their six room accommodations were just voted one of the 10 best tiny hotels in the world. After sleeping in with style, take a 2.7-mile walk above the city on the newly constructed Bloomingdale Trail (The 606). Originally a train route that began just after the Great Chicago Fire, this stretch of old train line is now a biking, running and community trail. Now that you’ve worked up an appetite, you’re ready for an early dinner at Fat Rice, a recent Bon Appetit pick for the 4th best new restaurant in America. It’s best to get there early, before the line curves around the block. After you’ve had your fill of Euro-Asian comfort food, slurp down a few beachy cocktails at the fabulously tiki-inspired Lost Lake. Complete your evening with a late night movie at the Logan Theatre, recently restored to its 1915 glory.

LOST LAKE - The best tropical drinks EVER! Watch out, they are strong!

LOST LAKE – The best tropical drinks EVER! Watch out, they are strong!

Explore Pilsen: If you’re actually an artist, love vintage and are fluent in Spanish – try Pilsen. Start your day trip with a unique visit to the National Museum of Mexican Art, where you’ll be immersed in the richness of Mexican art and culture. From textiles and folk art, to photography and sculpture – you’ll be sure to connect to an exhibition on a personal level. Then get in a little retail therapy with shops on 18th Street. A favorite for vintage, handmade and mid-century lovers is Modern Cooperative, which has a great mix of vintage furniture and clothing with modern gifts and accessories. For dinner, grab a seat at Simone’s Bar & Grill and get a real feel for the neighborhood crowd while eating pub food and drinking some local craft beers. Make sure to book tickets for a concert or performance ahead of time at Thalia Hall, a recently converted historic landmark turned music venue, cocktail bar and restaurant.

Modern Coop is the perfect spot for vintage, mid-century, gifts and more!

Modern Coop is the perfect spot for vintage, mid-century, gifts and more!

Explore Oak Park: If you’re a young family inspired by architecture and tranquil tree-lined streets – try Oak Park. Head out to Oak Park on the Chicago el train. The green line el tracks will take you directly to downtown Oak Park, where you can walk from cute shop to cute shop on cobblestone streets. You’ll end up right near Greenline Wheels, where you can rent bikes for the day and pedal your way over to Frank Lloyd Wright’s Home and Studio. You can stay for the indoor tour, or participate in the Frank Lloyd Wright Trust’s guided bike tour of more than 20 historic Wright-designed structures. Don’t forget to pack a picnic beforehand with the best cheese and accouterments from the delicious Marion Street Market.

Frank Lloyd Wright Home and Studio - Oak Park

Frank Lloyd Wright Home and Studio – Oak Park

Explore Evanston: If you’re into the college town vibe and spending a sunny day at the beach – try Evanston. With five public swimming beaches along Lake Michigan, Evanston is the perfect spot for a warm summer day in Chicago. After getting your suntan at the beach, head back to your quaint B&B the Lang House Chicago, complete with a spa and sauna for some extra R&R. Then it’s on to the dinner at the eclectic, delicious and highly-acclaimed Found Kitchen, on a nice night, ask to dine outside at their Parisian-style sidewalk café. Don’t forget the cocktail menu, the drinks are delicious!

Gorgeous Lake Michigan!

Gorgeous Lake Michigan! Photo credit:

The Lang House B&B - modern and elegant

The Lang House B&B – modern and elegant

Explore Hyde Park: If your idea of a good time is exploring one of the largest science museums in the Western Hemisphere and packing a little history lesson in too – try Hyde Park. Start your day by strolling along 53rd Street and visiting some of the local merchants. You can even try President Obama’s said favorite restaurant (cafeteria style) Valois Restaurant. From 53rd Street walk south toward the Midway Plaisance, which is the original midway from the 1893 World’s Columbian Exposition held in what is now Jackson Park. On the way, you’ll pass through the beautiful University of Chicago Campus. Head east down the midway towards the Museum of Science and Industry, and don’t miss a stroll in the Osaka Garden. This Japanese stroll garden features a series of water fountains, bridges and ornate stone-cut Japanese lanterns.


Osaka Garden part of historic Jackson Park

Explore Lincoln Square/Ravenswood: If your idea of a good time is beer, beer, beer and whiskey – try Lincoln Square. First, get yourself a group of friends and suite or two at the posh Guesthouse Hotel. You’ll need a place to call home after your day of gallivanting, and better that it’s your home away from home. Enjoy the delicious local beer selection at Half Acre Tap Room and take a tour of the brewery for another $10. Keep the craft beer theme going and try out the new, community-supported brewery and tap room at Begyle Brewing. If whiskey is more your speed don’t miss Koval Distillery. Chicago’s first working distillery since the mid-1800s this spot is truly artisan grain-to-bottle whiskey. Their tour and whiskey samples will keep you in your happy place for a few more hours. After all the drinking, you’re going to need some food and what’s better than pretending it’s Oktoberfest at the Chicago Brauhaus. Serving up German specialties and drinks, you can eat all the headcheese and bratwurst your heart desires.


Koval’s tours and cocktail classes are so much fun!

Have fun exploring Chicago! XO – Claire

  1. allie says:

    Great ideas! I visited that greetings from Chicago sign for a blog photo shoot!

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Meet Claire

Claire’s creative energy comes from her unique perspective on the world as both a trained interior designer and a passionate yoga teacher. Her affinity for kitchen design, timeless style and eclectic decorating are shared here, along with lots of interior design education and tips. Thanks for being here, please enjoy!

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