1/2

URBAN EXPLORER

Run, bike & kayak with this 3-day Chicago sightseeing itinerary: The 606, Maggie Daley Park, Chicago Riverwalk & more.

Back to Previous Page

Heart-pumping thrills in the heart of the city? You bet — Chicago is the perfect place to tap into your inner adventurer. Here are three full day's worth of sightseeing suggestions sure to raise your pulse.

The 3-day Chicago itinerary packs in new sights like The 606 and the outdoor climbing wall at Maggie Daley Park, plus Chicago essentials like The Lakefront Trail, beaches and the expanded Chicago Riverwalk. Not to mention eating and exploring great neighborhoods like Lincoln Park and Humboldt Park

 Urban Explorer 3-Day Chicago ItineraryClick to view full size map

DAY 1: Hightail it to Humboldt Park via The 606

At Hotel Lincoln, their tagline invites you to "live, stay and play like a local." Start with an early light breakfast on-site at Elaine's Coffee Call. Then hop on one of the hotel's complimentary townie bikes. You're headed a few miles west on Armitage to The 606, an old rail line recently transformed into a 2.7-mile elevated trail. When you reach the end, head back toward Humboldt Park for an impromptu picnic. On the west side of the park, look for the La Bomba Place food truck, which serves up massive Puerto Rican lechon sandwiches with mounds of fragrant rice. There's a small grassy hill near the truck, where you can enjoy a terrific view of the city. After exploring the lagoon and trails, ride to Parson's for frozen cocktails on the patio.

 

DAY 2: Catch lakefront views & tackle climbing walls among skyscrapers

Spend the morning running or skating along The Lakefront Trail. Get vertical on the climbing wall at Maggie Daley Park or, for more of a challenge, head to 31st Street Harbor for a stand-up paddleboard yoga class. Refuel at Green City Market, a sustainable and seasonal farmer's market in Lincoln Park. Toast the day's exploring with a craft cocktail on the rooftop at J. Parker, home to all-season views with their retractable glass enclosure.

 

DAY 3: Kayak through a canyon of architectural gems

Start your day off with a relaxing, farm-inspired brunch at Perennial Virant. Bike to the Chicago Riverwalk for a guided urban kayak tour along the Chicago River.

Enjoy pared down French cuisine al fresco at Cyrano's on the Riverwalk and then walk around the tranquil Alfred Caldwell Lily Pool before making your way to North Avenue Beach for incredible skyline and lake views.

Dinner is at Lincoln Park's North Pond, where chef Bruce Sherman serves fresh fare in a cozy arts and crafts bungalow.

 

+ BONUS ADD ON: Summer sweat in the park

For those who like to take workouts along on vacation, Chicago makes it easy with a free summer workout series at Millennium Park on the Great Lawn. Saturdays June through September, you can get your glow on with 45-minute sessions every hour on the hour from 7 to 10 a.m. Choose from tai chi, yoga, pilates and Zumba®; some classes are accompanied by live music or drumming for extra get-moving mojo.


Perennial Virant
1800 N. Lincoln Ave.
Chicago, IL 60614
(312) 981-7070
Hotel Lincoln
1816 N. Clark St.
Chicago, IL 60614
(312) 254-4700
Chicago Water Sport Rentals at 31st Street Harbor
3155 S. Lake Shore Dr.
Chicago, IL 60653
(312) 924-7994
Maggie Daley Park
337 E. Randolph St.
Chicago, IL 60601
(312) 742-3918
Chicago Riverwalk
376 N. Michigan Ave.
Chicago, IL 60601
Chicago's Lakefront Trail
300 S. Lake Shore Dr.
Chicago, IL 60605
Featured Partners
Book a Trip
Find Hotels In
Check In
Check Out
Rooms
Travelers
From
To
Depart
Return
Travelers
Flying From
Find Packages In
Check In
Check Out
Rooms
Travelers
From
To