Escape to Chicago

Escape to Chicago Chicago CVB

In the shadow of a giant Picasso statue on Chicago’s Daley Plaza, cyclists gather. It’s late afternoon on a gorgeous Friday in April. 

As my friend, Wendy, and I ride up on our rental bikes, 50 cyclists are hanging out, waiting. Soon the number swells to 100, 200, 300, maybe more. A reporter from the local TV station interviews a wild-haired twenty-something, whose kooky bike towers ten feet high. Somebody hands us a yellow map and says, “Happy Friday.” Nearly everyone is smiling.

College kids sporting colorful tattoos seem to be in the majority, but Wendy and I aren’t the only middle-agers around. There are even a few helmeted kids with their parents, ready to roll. People are chatting, meeting up with friends. Everyone has a bike—some fancy, most not. The noise level gradually increases from a hum to a mellow roar. Cops roll up on motorcycles, revving up their engines, and hang around the edge of the square, looking important.  

Wendy and I strike up a conversation with a guy our age named Daniel, who has a wild gleam in his eye and tells us we should come back for the Bike Naked Ride. “It’s a blast,” he says grinning. Someone rides by pulling a cart with speakers blaring music. The energy in this place is palpable. You can feel it in your skin. It’s electric. 

Soon a few cyclists start circling the block. Slowly others hop on their bikes and merge into the growing throng of two-wheelers. Wendy and I roll right into the street and begin circling the block, one, two, three times. We’re bumper to bumper with other bikes. The traffic gives way as the group grows. Finally the ride begins, motorcycle escorts helping clear the path. The leaders of the pack head west on Randolph Street, and we follow, our legs pumping the pedals as the evening breeze washes over us. Wheee!

Welcome to Chicago Critical Mass, a once-a-month gathering of cycling aficionados who celebrate two-wheeling.

Wendy and I visited Chicago last spring for a big-city girlfriend getaway. While doing my pre-trip research, I stumbled upon this event, which takes place the last Friday of every month. It seemed the perfect opportunity to connect with locals and see the city from a unique perspective. And it absolutely was. Unfortunately, by the time the Critical Mass finally started moving, Wendy and I could only ride for a few blocks before we had to make a U-turn back to the bike rental shop, which closed at seven. Oh well, it was fun while it lasted.

Though it was only our first day, Wendy and I already knew Chicago was the perfect place for a city getaway. Even though neither us has ever lived in a big city, something about Chicago made us feel right at home. Maybe it’s the ubiquitous Lake Michigan, which astonished us with its tranquil beauty and aquamarine hues. Maybe it’s Grant Park with its luscious green spaces, fountains, statues, and towering trees. Maybe it’s the wide sidewalks and avenues that somehow made the tallest buildings feel less forbidding, friendlier. Or maybe it’s the people, whose Midwestern charm and down-home friendliness strike you as oddly endearing in a big-city setting. Whatever the reason, Wendy and I found Chicago very easy to like.  

We planned an amazing itinerary, enabling us to experience a week’s worth of Chicago in half the time. We stayed in three cool accommodations, ate in a variety of Chicago’s hip restaurants, swooned in a sumptuous spa, and explored the city’s rich cultural scene. After arriving on a nonstop flight from Norfolk Friday morning, we hit the ground running and didn’t stop until we collapsed on the plane ride home Monday afternoon. For four days and three nights, Wendy and I made the most of every moment in this delightful city. Now, thanks to all our efforts, you can plan your own visit, and you don’t even have to do any research. Here are our recommendations for what to do, where to eat, and where to stay.


• Millennium Park – Opened in 2004, this park borders the Magnificent Mile and features the Pritzker Pavilion, a concert venue designed by Frank Gehry with billowing steel ribbons surrounding the stage, and Cloud Gate—more popularly known as the Bean—a silver sculpture as big as a spaceship that pulls tourists to its gleaming, shiny surface like a magnet. TIP: Rent a bike from Bike and Roll Chicago located at Millennium Park. Even if your trip doesn’t coincide with a Critical Mass event, you’ll enjoy biking to museums along the waterfront.

• Chicago Architectural Foundation – Known as the birthplace of skyscrapers, Chicago also has a reputation as a very green city. Wendy and I attended a “Green Inside Out” tour with CAF and learned about ways buildings—old and new— emphasize eco-friendly techniques. For example, the Santa Fe Building, built in 1903, features a central light well, which allows natural light to penetrate the building’s interior. Newer buildings incorporate the latest energy-saving devices, such as lights that automatically dim as daylight increases. TIP: CAF’s Architecture River Cruise has been voted the city’s #1 architecture tour and covers more than 50 sites and buildings.

• Museum of Science and Industry – Wendy and I could have spent days in this museum, the largest science center in the Western Hemisphere, located about four miles from downtown. On exhibit through January is “Smart Home: Green + Wired,” a three-story, fully functioning, sustainable home in the museum’s backyard. One innovation, the energy dashboard, provides real-time data showing how much energy the solar panels generate compared to how much the home uses. TIP: Don’t miss the “Fast Forward: Inventing the Future” exhibit, where you’ll learn about cutting-edge inventors from around the world who are finding new ways to solve problems.

• The Museum Campus – Within walking (or biking) distance of downtown, the Museum Campus includes the Shedd Aquarium, the Adler Planetarium, and the Field Museum, founded by none other than Marshall Field. A few years ago I visited these museums and always wanted to return. Unfortunately, Wendy and I could only enjoy a brief visit to these venues, which deserved more time than we could spare. TIP: Visit Sue, the world’s largest, most complete Tyrannosaurus Rex in the Field Museum.;;

• John Hancock Observatory – This must-see attraction offers amazing views of Lake Michigan and the Chicago skyline from 1,000 feet in the air. The Visitor’s Center (on the top floor, of course) offers exhibits detailing the city’s history, a café, and gift shop. Unfortunately, it poured rain during Wendy’s and my visit, but we enjoyed the experience nevertheless. TIP: An entertaining multi-media sky tour, narrated by David Schwimmer, is included with your ticket; kids’ and adults’ versions are available.

• Art Institute of Chicago – One of the world’s finest art museums, the Art Institute features an amazing collection of American art, including Grant Wood’s “American Gothic.” Wendy and I were lucky to view a Edvard Munch exhibit that included works by Munch and his peers. We just missed visiting the new Modern Wing, which opened in May, a good reason to return. TIP: Don’t miss the Thorne Miniature Rooms, an exhibit of dollhouse-sized European interiors with exquisite detail and beauty.


• Osaka Sushi – One of my favorite things to Google before I visit a new city is Cheap Eats. In Chicago a sushi restaurant on Michigan Avenue came up, and Wendy and I decided to try it for lunch on Friday. As soon as we saw people lining up for this take-out venue, we knew it had to be good. And it was. TIP: Try the Hawaii roll with mango. It’s a party in your mouth!

• Mercat a la Planxa – Friday night we dined in one of Chicago’s newest restaurants, and judging from the chic, well-dressed crowds, it’s already making its mark. As the name suggests, Catalan-inspired cuisine is the order of the day. Wendy and I swooned at the amazing jamon iberico de bellota, a smoky ham that melted in your mouth. Chef Jose Garces treated us to a variety of his signature dishes including beef shortribs, butternut squash dumplings with lamb ragout, and butter-poached lobster. Absolutely everything was divine. TIP: Order the potatoes with spicy paprika aioli for a taste sensation!

• The Gage – A convivial spot across from Millennium Park, The Gage struck me as a sophisticated tavern, where apron-clad waiters bustled about attending to diners’ every need. My cousin’s wife, Val, a Chicago native, met Wendy and me for lunch at The Gage, and Val said it was a favorite spot for business lunches. We shared an incredible array of upscale comfort food: a salad that featured seared sea scallops and grilled red onion, another salad topped with peppered Angus hanger steak, and a signature dish of crispy skin whitefish. TIP: Try The Gage N-17 Fondue, a rich, creamy combination of butter kaase, brie, spinach and toast.

• Markethouse Restaurant – A new dining destination, the Markethouse specializes in fresh, local, seasonal dishes rooted in the Heartland, but with surprising twists. For example, as an appetizer Wendy and I shared an artichoke tart served with olive oil jam, a savory, sweet combination. For my entrée, I tried Colorado lamb rack, succulent and juicy, and Wendy enjoyed a fried green tomato salad with smoked trout. TIP: Try the wild ramps sautéed with smoked bacon. Mmmm.

• Rockit Bar & Grill – I’ve been to many a breakfast brunch in my day, but Rockit’s is my favorite, hands down. The restaurant has a sports-bar vibe, but way classier. After the waitress brought our Bloody Marys, served in a glass mug, Wendy and I headed to the build-your-own gourmet Bloody Mary bar, where dozens of embellishments awaited—roasted garlic, shrimp, an array of olives, pickles, celery, salami, cheese—you name it. You could almost make a meal out of it. But don’t. You have to try the Rockit Burger, named Best Burger by Good Morning America: kobe beef, melted brie, fried shallots, medjool date aioli, and truffle fries. It’s big enough to share and powerfully good. TIP: You must try the sweet potato fries sprinkled with brown sugar—to die for.

• ajasteak – This was our favorite restaurant of the trip, and as you can tell, it was hard to pick. The Asian-inspired décor, the incredible food, and the friendly service added up to a perfect evening. We started with a colorful array of sashimi—golden big eye snapper, Hawaiian yellowtail, and Japanese red snapper—accompanied by a maki roll with tuna caviar. And yes, as you’d expect, the steak is incredible here (get the kobe beef—you deserve it)—but don’t miss the slow-roasted sea bass or the Chef Josh Linton’s signature braised beef short ribs. TIP: Order the stellar salad called kinalau with marinated yellowfin and greens in a light coconut-milk dressing. Wendy and I decided it was the best we’d ever eaten. (I have the recipe; email me at This email address is being protected from spambots. You need JavaScript enabled to view it. if you’d like a copy).


• Blackstone Renaissance – Overlooking Grant Park, you can’t ask for a more central location than the Marriott Blackstone, which incidentally made Conde Nast’s Hot List this year. Built in 1910, the hotel was recently refurbished and its rooms are bright, modern, and comfortable. Mercat a la Planxa (see above) is the property’s on-site restaurant.

• Amalfi Hotel – This European style hotel welcomes you into its chic lobby with aromatherapy, a lovely citrus scent. We loved the hip décor and comfy beds. Every afternoon from 5:30-7 p.m. guests are invited to enjoy complimentary beverages and appetizers in the Ravello Lounge.

• The dana hotel and spa – A luxury boutique hotel (and home of ajasteak—see above), the dana impressed us with its light, airy rooms and industrial-chic décor. Both the hotel and the Vertigo Sky Lounge made Conde Nast’s Hot List, deservedly so.

• Felix Hotel – While we didn’t stay at this new property, I checked it out because of its green construction materials and commitment to energy efficiency. In fact, Hotel Felix is Chicago’s first hotel to receive Silver LEED Certification. While its décor utilizes organic materials, a comfortable elegance imbues the surroundings.

• Trump Tower – We took a tour of this luxury high-rise property, which features both apartment living and hotel rooms and suites, and found it a perfect option for families. The spacious rooms feature a kitchenette, marble bathrooms, and gorgeous views of the Chicago skyline.


• Buddy Guy’s Legends – You can’t visit Chicago without experiencing live music. Wendy’s a blues fan, so one night we headed to the inimitable Buddy Guy’s Legends, where we moved and grooved to some soulful sounds.

• Andy’s Jazz – A favorite for jazz aficionados since 1951, Andy’s features a variety of genres—traditional, swing, bebop, fusion, Latino, and Afro-Pop. We visited this casual venue on a Sunday evening for Andy’s Jam Session. It was crazy, daddy-o.

Our weekend wound down in one of Chicago’s fanciest addresses, Trump International Hotel and Tower, where Wendy and I spent an hour or so Monday morning luxuriating in the spa. Afterwards we lunched in Sixteen, theproperty’s signature restaurant overlooking Lake Michigan, where a delicious lunch fortified us for the flight home. Sixteen recently opened an outdoor terrace, appropriately named the Terrace, where al fresco dining will be available seasonally.

Riding back to O’Hare in the “El,” Chicago’s efficient metro system. Wendy and I were quiet, deep in thought. Our senses were depleted after having experienced such a whirlwind tour of Chicago, but both of us knew, without even saying it, that Chicago would always be a special place for us, one I’m sure we’ll revisit one day.

And you know what? Everything we did on this trip, I would do all over again and not be bored one bit. From the Critical Mass on Friday to Andy’s Jazz on Sunday, Wendy and I made sure every moment mattered. And isn’t that something we all need to be reminded of now and then? To pay attention—even when we’re home in familiar surroundings—and make each precious moment count.

Visit for information.

Peggy Sijswerda

Tidewater Women Magazine, Editor & Co-Publisher.

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