Chicago: Three Days, Three Ways

Chicago is known for its dramatic architecture, which soars above an otherwise flat landscape. But there’s also plenty to check out on the ground. Here, we’ve got three amazing ways to see the city from a whole new vantage point.

Pedal Across the City

With over 2,500 light blue Divvy Bikes parked around town, it’s easy to explore via cycle. For $7 you get 24 hours of unlimited 30-minute rides. Download the app CycleFinder, which will help you locate the nearest station. Here, the perfect cycling itinerary.


Divvy Bikes, available throughout the city. (Photo: Daniel X. O’Neil)

Stop 1: Millennium Park British artist Anish Kapoor’s the Bean (aka Cloud Gate) is highly photographed. But don’t skip Millennium Park’s other cool sights: the two 50-foot glass towers of Crown Fountain, the stunning BP Pedestrian Bridge, the ultra-modern Lurie Garden, and Jay Pritzker Pavilion, which hosts free concerts.


A high-tech stairway at the Art Institute of Chicago. (Photo: Michelle Lee)

Stop 2: The Art Institute of Chicago This world-renowned museum is a must for its contemporary-art collection—and it’s easier to navigate than many institutions in the same league. Download their AIC Tours app to create a customized tour. And check out the Thorne Room Miniatures—perfect for anyone who has ever owned a dollhouse. For stunning views, lunch at Terzo Piano, in the museum’s Contemporary Wing, can’t be beat. Another option: The Gage, just across Michigan Avenue. Order the What Diet Burger—and keep on biking.

Stop 3: Navy Pier Touristy, but worth it, Navy Pier has a convenient Divvy station. Lock your bike and stroll along the pier’s north side for breathtaking views of Chicago, followed by a visit to the gorgeous Smith Museum of Stained Glass Windows.


A Chicago Water Taxi tour of the river. (Photo: Sean Hayford O’Leary)


(Photo: Seth Anderson)

Hit the Waves

One of the most amazing ways to see the Windy City is on the water—the key is finding the boat that fits your personality. If you’re traveling with teens and tweens, Seadog Cruises has hilarious docents, including a cruise up the river, then a speedboat ride on the lake. Perfect for design buffs: the Chicago Architecture Foundation River Cruises, led by CAF docents who have in-depth knowledge of its buildings and architects. If you’re more active, try kayaking with Wateriders, which offers guided themed tours—from architecture to ghosts to gangsters—and even a night paddle to watch the fireworks at Navy Pier. Or opt for the universal (and affordable) favorite: the Chicago Water Taxi. You can get an unlimited pass for $10 or purchase a single ride for $3 weekday/$4 weekend. One top stop: the Ogilvie Transportation Center, which is convenient to the French Market. Grab croissants from Delightful Pastries. Or if you’re swinging by closer to lunch, there’s Little Goat Bread, Saigon Sisters, or Pastoral Artisan, for amazing sandwiches.


Nam Khao, made with bacon laab, toasted rice, kaffir, fermented pork, and endive at Saigon Sisters, in the French Market. (Photo: opacity)

Hop on a Segway

There’s no better—and easier way—to see the city than with Chicago Segway Tours, which offers a number of easy explorations, from a gangster-themed itinerary to a tour of haunted Chicago—scoping out the results of deaths and disasters, murderers and murderesses. One of of our favorite expeditions zips you from Navy Pier north along the lake to the Lincoln Park Zoo. On the way you’ll pass Chicago’s favorite beaches (yes, the sand is natural) on the Gold Coast, then zoom by the original Playboy mansion.


On a roll in Chicago. (Photo: Franca Leyendecker)

The company will also customize trips—ask for a night tour that includes one of Chicago’s most awe-inspiring look outs, Willis Tower, where you can experience Skydeck, an enclosed glass ledge that extends out from the building 1,353 feet in the air. Word of warning: it isn’t for anyone with a fear of heights. After, for lunch and all things Italian, head to Eataly: two stories of pasta, cheese, focaccia, gelato, wine, and an in-house brewery. Just the thing to calm your nerves after the 103rd floor.


A bird’s-eye view from the Skydeck. (Photo: Jamie McCaffrey)

Where to Stay

These three hotels celebrate Chicago’s architectural heritage—and they all feature great water views.

The Langham, Chicago: In a newly renovated Mies van der Rohe building, this luxury hotel has posh rooms and a great restaurant, Travelle.

Trump International Hotel and Tower: Stay here for the floor-to-ceiling vistas, modern décor, and an amazing spa.

Radisson Blu Aqua Hotel Chicago: A more affordable option, in a building designed by architect Jeanne Gang.


(Courtesy: The Langham Chicago)

Where to Eat

Chicago is a foodie town, and these restaurants combine talented chefs and dramatic interiors—the perfect ending to an active day.

The Boarding House:Master sommelier Alpana Singhamazing’s wine list complements chef Tanya Baker’s fresh take on American classics.

Japonais by Morimoto: Right on the river, this restaurant has been reborn, thanks to the Iron Chef’s innovative menu.

Nico Osterio: Rustic Italian seafood, with a stunning wall of foliage as a backdrop.

Laura Hine is the curator and editor of, a neighborhood-by-neighborhood look at interesting boutiques in Chicago.