Rooftop bars, kayaking and tacos at the beach: A blueprint for a Chicago adventure

Dawn Gilbertson, USA TODAY

CHICAGO — The last time my son and I roamed this sparkling lakefront city together, he was wearing a Minnesota Vikings Santa hat and matching pajama pants and getting heckled at Soldier Field.

It was a surprise trip to celebrate his 11th birthday, tickets to a Chicago Bears-Vikings showdown as the main attraction. (The Vikings lost.)

Fast forward nearly nine years. We reprised the mother-son adventure a few weeks before he starts back to college in Arizona and three months after I moved here as an empty nester.

Jack and I traversed the city for four days, logging nearly 40 miles on foot and bike. It was more about spending time together outside – something not possible in Phoenix in the summer – than it was about checking off every tourist attraction and deep dish pizza place. We'd already hit most of the latter on a family fall break trip when he was in grade school.

It started with decadent cheeseburgers on the patio at Small Cheval in Old Town, an offshoot of the hard-to-get-into Au Cheval, and ended with a toast at the lake before his flight.

The menu at Small Cheval in Chicago's Old Town, a casual offshoot of popular Au Cheval, is painted on the wall outside.

The highlights:

Biking the lakefront

Unless it's Polar Vortex season, no trip to Chicago is complete without a bike ride, run or stroll along Lake Michigan.

We rented Divvy Bikes, Chicago's bike-share program, from a dock in Old Town and headed north to Lincoln Park and a bridge to the 18-mile lakefront trail. It's $15 for a 24-hour pass, and you can drop it off at any other station with open slots. Note that a city project completed in 2018 separated the bike and pedestrian lanes, so make sure you're in the correct lane.

We headed north, stopping for more skyline photos than he would have liked, and one bike swap because of a loose pedal.

There are a handful of waterfront restaurants and bars along the way, but he zeroed in on a tiny taco stand near Waveland Park and the lakefront Sydney Marovitz Golf Course. We ordered four street tacos from Two Wheels Taco: two chicken and two carne asada and took them and our bikes to the lake for a picnic.

It was the perfect pit stop.

Jack Gilbertson enjoying lakefront street tacos from Two Wheels Tacos during a bike ride on Chicago's Lakefront trail.

We kept going north, before turning back and docking the bikes near Ohio Street Beach so we could walk back to Old Town via the shopping Mecca that is Michigan Avenue.

Our self-guided bike tour was about 3.5 hours long.

The next morning, with a little time left in our 24-hour pass, we picked up bikes and headed to the Chicago Riverwalk, where we planned to rent kayaks.

One wrinkle: It was a weekday morning and several stations we stopped at along the way were full of bikes. We finally found a drop-off spot in The Loop, the downtown business district, and walked to the riverwalk.

Kayaking the Chicago River

USA TODAY travel reporter Dawn Gilbertson and her son, Jack, kayaking on the Chicago River.

The Chicago River is a busy thoroughfare, with giant tour boats and pleasure boats galore, especially in the summer.

I've kayaked a couple of times previously, but am a nervous novice so convinced my son to do a tandem kayak so I didn't veer into the path of a Chicago architecture tour.

We rented one from Urban Kayaks and, after a quick test of our paddling technique and very thorough safety video (stay away from the lake and hug the right side of the river in each direction, in the imaginary kayak "lane"), we were launched into the water for a one-hour ride.

I've seen Chicago and the river from many vantage points, but the kayak was the most unique and I wished we stayed on longer, intimidating as it was when sightseeing tours were looming. Next on my list: one of Urban Kayaks' fireworks, history or sunset tours.

My son described the experience as "freakin' cool'' and "an awesome way to see the city.''

We walked along the riverwalk and Wacker Drive to Wells Street Market, one of my favorite food halls in Chicago. (It's only open during the week.) I had gyros from Piggie Smalls Gyro Shop, a stand from the founder of esteemed Chicago restaurant Purple Pig, and Jack had a Nashville hot chicken sandwich from Fry the Coop

Rooftop views

Cindy's Rooftop, a restaurant and bar at the Chicago Athletic Association Hotel on Michigan Avenue near Millennium Park, rightfully ranks up there as a must-see in Chicago for sweeping views of the lake, the skyline and The Bean (official name "Cloud Gate") and Crown Fountain below.

The views from Cindy's Rooftop, a restaurant at the Chicago Athletic Association Hotel across from Millennium Park, are stunning no matter which way you turn.

We headed to the crowded outdoor bar and hovered for a spot against the railing for the perfect photo.

Our other "rooftop'' venue, albeit indoor and touristy: 360 Chicago on the 94th floor of the iconic John Hancock Building. We picked the Hancock because it was closer than the SkyDeck at Willis Tower (Sears Tower in another life.)

360 Chicago, an observatory, is on the 94th floor of the iconic John Hancock Building in Chicago.

It's nothing as fancy as the Signature Room a floor above or the Signature Lounge two floors above, but it's more family-friendly, the views are just as fantastic, there's a bar, and you get some history about the skyscraper. We scored a couple of living-room-like lounge chairs by the windows facing north and sat there for nearly an hour. We didn't try the Tilt, which is billed as "Chicago’s highest thrill ride, an enclosed moving platform that literally tilts you out over Michigan Avenue.''

Inspired by the lake views below, we ditched our dinner plans and headed to Oak Street Beach for a sunset picnic with cheese, salad and other snacks picked up at 1350 Commissary Market, tucked inside a residential high-rise on Lake Shore Drive.

Sunset on Oak Street Beach in Chicago

Lincoln Park Zoo

Zoos aren't at the top of most 19-year-olds' must-see lists in Chicago, but Jack was intrigued when he spotted a camel on our bike ride through Lincoln Park on the way to the lakefront trail.

We made plans to go back on his last day, after strolling through a farmer's market in Lincoln Park.

Animal lover or not, Lincoln Park Zoo is a must-see in Chicago. Think of it as a giant city park with animals and surprise views of the skyline. The best part: it's open every day, and admission is free.

The Chicago skyline from Lincoln Park Zoo, which is free and open every day.

We wandered for more than an hour, checking out a polar bear, giraffe, monkeys and more. 

As I was texting a friend for the name of his favorite hot dog stand (The Wiener's Circle), Jack jumped in line for a regular hot dog at the zoo. It wouldn't have been my choice, but this wasn't a trip about the best food spots in Chicago. 

He wolfed it down, and we walked back through Lincoln Park to Michigan Avenue for some back-to-school shopping.

This article originally appeared on USA TODAY: Chicago guide: Things to do in the Windy City from the zoo to kayaking