Wherever your pursuits lie, Chicago presents memorable issues so that you can see and do. These are 10 of one of the best.
10Greatest Editors, USA TODAY 10Greatest

CHICAGO — The final time my son and I roamed this glowing lakefront metropolis collectively, he was sporting a Minnesota Vikings Santa hat and matching pajama pants and getting heckled at Soldier Subject.

It was a shock journey to have fun his 11th birthday, tickets to a Chicago Bears-Vikings showdown the primary attraction. (The Vikings misplaced.)

Quick ahead almost 9 years. We reprised the mother-son journey a couple of weeks earlier than he begins again to school in Arizona and three months after I moved right here as an empty nester.

Jack and I traversed the town for 4 days, logging almost 40 miles on foot and bike. It was extra about spending time collectively outdoors — one thing not potential in Phoenix in the summer — than it was about checking off each vacationer attraction and deep dish pizza place. We might already hit many of the latter on a household fall break journey when he was in grade college.


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It began with decadent cheeseburgers on the patio at Small Cheval in Previous City, an offshoot of the hard-to-get-into Au Cheval, and ended with a toast on the lake earlier than his flight.

The highlights:

Biking the lakefront

Until it is Polar Vortex season, no journey to Chicago is full with no bike trip, run or stroll alongside Lake Michigan.

We rented Divvy Bikes, Chicago’s bike-share program, from a dock in Previous City and headed north to Lincoln Park and a bridge to the 18-mile lakefront trail. It is $15 for a 24-hour go, and you’ll drop it off at every other station with open slots. Word  metropolis undertaking accomplished in 2018 separated the bike and pedestrian lanes, so be sure to’re within the right lane.


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We headed north, stopping for extra skyline photographs than he would have preferred, and one bike swap due to a free pedal.

There are a handful of waterfront eating places and bars alongside the way in which, however he zeroed in on a tiny taco stand close to Waveland Park and the lakefront Sydney Marovitz Golf Course. We ordered 4 road tacos from Two Wheels Taco: two hen, and two carne asada and took it and our bikes to lake for a picnic.

It was the right pit cease.

We stored going north, earlier than turning again and docking the bikes close to Ohio Street Beach so we may stroll again to Previous City by way of the procuring Mecca that’s Michigan Avenue.

Our self-guided bike tour was about three.5 hours lengthy.

The subsequent morning, with just a little time left in our 24-hour go, we picked up bikes and headed to the Chicago Riverwalk, the place we deliberate to lease kayaks.

One wrinkle: It was a weekday morning and a number of other stations we stopped at alongside the way in which had been stuffed with bikes. We lastly discovered a drop-off spot in The Loop, the downtown enterprise district, and walked to the riverwalk.

Kayaking the Chicago River

The Chicago River is a busy thoroughfare, with large tour boats and pleasure boats galore, particularly in the summertime.

I’ve kayaked a pair instances beforehand, however am a nervous novice so satisfied my son to do a tandem kayak so I did not veer into the trail of a Chicago structure tour.

We rented one from Urban Kayaks and, after a fast take a look at of our paddling approach and really thorough security video (keep away from the lake and hug the suitable aspect of the river in every course, within the imaginary kayak “lane”), we had been launched into the water for a one-hour trip.

I’ve seen Chicago and the river from many vantage factors, however the kayak was essentially the most distinctive and I wanted we stayed on longer, intimidating because it was when sightseeing excursions had been looming. Subsequent on my listing: one in every of City Kayaks’ fireworks, historical past or sundown excursions.

My son described the expertise as “freakin’ cool” and “an superior strategy to see the town.”

We walked alongside the riverwalk and Wacker Drive to Wells Street Market, one in every of my favourite meals halls in Chicago. (It is solely open through the week.) I had gyros from Piggie Smalls Gyro Shop, a stand from the founding father of esteemed Chicago restaurant Purple Pig, and Jack had a Nashville sizzling hen sandwich from Fry the Coop

Rooftop views

Cindy’s Rooftop, a restaurant and bar on the Chicago Athletic Affiliation Lodge on Michigan Avenue close to Millennium Park, rightfully ranks up there as a must-see in Chicago for sweeping views of the lake, the skyline and The Bean (official title “Cloud Gate”) and Crown Fountain under.

We headed to the crowded outside bar and hovered for a spot in opposition to the railing for the right picture.

Our different “rooftop” venue, albeit indoor and touristy: 360 Chicago on the 94th flooring of the the enduring John Hancock Constructing. We picked the Hancock as a result of it was nearer than the SkyDeck at Willis Tower(Sears Tower in another life.)

It’s nothing as fancy as the Signature Room a floor above or the Signature Lounge two flooring above, but it surely’s extra household pleasant, the views are simply as incredible, there is a bar, and also you get some historical past concerning the skyscraper. We scored a pair living-room-like lounge chairs by the home windows going through north and sat there for almost an hour. We did not attempt the Tilt, which is billed as “Chicago’s highest thrill trip, an enclosed transferring platform that actually tilts you out over Michigan Avenue.”

Impressed by the lake views under, we ditched our dinner plans and headed to Oak Road Seashore for a sundown picnic with cheese, salad and different snacks picked up at 1350 Commissary Market, tucked inside a residential high-rise on Lake Shore Drive.

Lincoln Park Zoo

Zoos aren’t on the prime of most 19-year-olds’ must-see lists in Chicago, however Jack was intrigued when he noticed a camel on our bike trip by way of Lincoln Park on the way in which to the lakefront path.

We made plans to return on his final day, after strolling by way of a farmer’s market in Lincoln Park.

Animal lover or not, Lincoln Park Zoo is a must-see in Chicago. Consider it as a large metropolis park with animals and shock views of the skyline. The very best half: it is open each day, and admission is free.

We wandered for greater than an hour, trying out a polar bear, giraffe, monkeys and extra. 

As I used to be texting a buddy for the title of his favourite sizzling canine stand (The Wiener’s Circle), Jack jumped in line for an everyday sizzling canine on the zoo. It would not have been my alternative, however this wasn’t a visit about one of the best meals spots in Chicago. 

He wolfed it down, and we walked again by way of Lincoln Park to Michigan Avenue for some back-to-school procuring.


Chicago’s Lincoln Park Zoo welcomed an endangered Western Lowland Gorilla born on Mom’s Day to 22-year-old mother Rollie. The latest addition, a male, has but to be weighed, measured or named. (Could 14)

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