Nature Boardwalk is one of The 15 Best Hiking Trails in Chicago.

1. Nature Boardwalk

9.3
2001 N Clark St (btwn W Fullerton Pkwy & LaSalle Dr), Chicago, IL
Hiking Trail · Lincoln Park · 22 tips and reviews

Jonathan F.Jonathan Ferrera: Chicago's beautiful South Pond. A wonderful place for a stroll to see turtles, bluegill, herons, and ducks. It really bursts to life in the summer.

Hazel G.Hazel Garcia Cristan: A Park worker told me the composite boards get very HOT ... especially on days with no cloud cover ... so avoid walking your dog here on very hot sunny days to protect his paws.

Jess B.Jess Battoe: Absolutely beautiful on a cool day.

Bloomingdale Trail — The 606 is one of The 15 Best Hiking Trails in Chicago.

2. Bloomingdale Trail — The 606

9.3
Bloomingdale Ave, Chicago, IL
Hiking Trail · Bucktown · 26 tips and reviews

Kevin M.Kevin M. McNally, CMP: Ideal place to walk, run, ride a bike in Wicker Park, Bucktown, Logan Square neighborhoods. You'll see art installations and (seasonal) art and yoga events. One of many Chicago parks to enjoy!

Rick T.Rick Torres: Side lanes are padded which my knees love. Trees are still young so shade is rare. Bring sunglasses or even a hat. Still is a work in progress. Can't wait to see the finished park.

Stellaa D.Stellaa Duhart: In the summer it gets pretty busy with runners, bikers and skaters.

The 606 — Eastern Terminus is one of The 15 Best Hiking Trails in Chicago.

3. The 606 — Eastern Terminus

9.1
1806 N Ashland Ave, Chicago, IL
Hiking Trail · Bucktown · 6 tips and reviews

Nicolas H.Nicolas Hernandez: Great way to see the neighborhood from a different perspective. Enjoy the great businesses just off the 606.

Thierry L.Thierry Levenq: It’s nice but there is no comparison whatsoever with the highline in New York.

VV: Amazing for walking/running/biking!

The 606 — Western Terminus is one of The 15 Best Hiking Trails in Chicago.

4. The 606 — Western Terminus

9.1
Ridgeway & Bloomingdale, Chicago, IL
Hiking Trail · Logan Square · 7 tips and reviews

Stellaa D.Stellaa Duhart: A really nice urban trail to run, skate or bike. In summer it gets really busy.

GeorgeGeorge: Lots of smiling faces on this trail 😊🚴

Paige K.Paige Kaliski: bike here at night... it feels like you're in a dream

Lakefront Trail is one of The 15 Best Hiking Trails in Chicago.

5. Lakefront Trail

9.5
Lake Michigan Lakefront (at N Lake Shore Dr), Chicago, IL
Hiking Trail · Grant Park · 132 tips and reviews

Zach S.Zach Solomon-Beloin: This trail is one unique aspect that separates Chicago from other cities. Great to run and enjoy amazing views of the lake and city.

Dorothy C.Dorothy Crawley: Water clears your mind, body and soul

USA TODAYUSA TODAY: This paved, 18-mile path along scenic Lake Shore Drive is often packed with joggers, bike commuters and tourists alike. Read more.

The 606  / Midpoint is one of The 15 Best Hiking Trails in Chicago.

6. The 606 / Midpoint

8.9
(Washtenaw), Chicago, IL
Hiking Trail · Logan Square · 3 tips and reviews

Michael H.Michael Haarala: Beautiful trail for walking and biking. One of the best ways to see the neighborhoods around it!

Amy R.Amy Robertson: Busy on weekends!

Fallon L.Fallon Leyba: great view

Lake Michigan Running Path is one of The 15 Best Hiking Trails in Chicago.

7. Lake Michigan Running Path

8.4
Chicago, IL
Hiking Trail · Lincoln Park · No tips or reviews
Caldwell Woods Bicycle Trail (North Branch Trail) is one of The 15 Best Hiking Trails in Chicago.

8. Caldwell Woods Bicycle Trail (North Branch Trail)

8.4
N Caldwell Ave (W. Devon Ave), Chicago, IL
Hiking Trail · Wildwood · 5 tips and reviews

Nery E.Nery Encarnacion: The best paved trail in Chicago!

Cristina B.Cristina Barroso: Nice trail. Very convenient access to and from Milwaukee Ave. and it even takes you all the way to the Chicago Botanic Gardens. Brilliant.

Lina G.Lina Gonzo: Take this trail north all the way to the Chicago Botanic Gardens (and back)!

Bloomingdale Trail - Albany Whipple Park Entrance is one of The 15 Best Hiking Trails in Chicago.

9. Bloomingdale Trail - Albany Whipple Park Entrance

8.2
1803 N. Albany Avenue (at Bloomingdale Avenue), Chicago, IL
Hiking Trail · Logan Square · 1 tip

Joan V.Joan V: A great way to get to Ashland from Humboldt Park with no traffic and a bit of nature :)

Shamrock Shuffle Start Line & Corrals is one of The 15 Best Hiking Trails in Chicago.

10. Shamrock Shuffle Start Line & Corrals

8.0
Chicago, IL
Hiking Trail · Grant Park · 1 tip

Ramel W.Ramel Werner: Always a great day for running.

Montrose Harbour (CARA MTP) is one of The 15 Best Hiking Trails in Chicago.

11. Montrose Harbour (CARA MTP)

8.0
Chicago, IL
Hiking Trail · Uptown · 2 tips and reviews

Roman W.Roman Warren: Cara group leaders are awesome!!

Chris V.Chris Varner: The Color Run!

Bill Jarvis Migratory Bird Sanctuary is one of The 15 Best Hiking Trails in Chicago.

12. Bill Jarvis Migratory Bird Sanctuary

8.1
3400 N Lake Shore Dr, Chicago, IL
Hiking Trail · Lakeview · 1 tip

Amy K.Amy K: Lots of benches to sit and enjoy the birds and scenery. You can bring your leashed dogs too!

Lincoln Park Trail is one of The 15 Best Hiking Trails in Chicago.

13. Lincoln Park Trail

7.5
Hiking Trail · Lake View East · 2 tips and reviews

Saif D.Saif Dia: Don't be afraid of the dragonflies in the summer

Meghan P.Meghan Preuss: Beautiful running through Lincoln Park and along Chicago’s lakefront!

Chicago Riverwalk is one of The 15 Best Hiking Trails in Chicago.

14. Chicago Riverwalk

9.4
Chicago River, Chicago, IL
Waterfront · The Loop · 139 tips and reviews

SSK016SSK016: Very alive ❤️ great for boat rides ,walk , restaurants and in the heart of the city .

Chicago Park DistrictChicago Park District: Urban Kayaks are open for the season! Located at 270 E. Riverwalk South. Mon - Fri 10 a.m. - 6 p.m. and Sat - Sun 9 a.m. - 5 p.m. (312) 965-0035 http://urbankayaks.com/

Travel + LeisureTravel + Leisure: For the first 10 minutes of each hour during the day, Centennial Fountain at the east end shoots water in a great arc across the river. Read more.

Maggie Daley Ice Skating Ribbon is one of The 15 Best Hiking Trails in Chicago.

15. Maggie Daley Ice Skating Ribbon

8.8
337 E Randolph Dr (Columbus Drive), Chicago, IL
Skating Rink · Grant Park · 19 tips and reviews

Jonathan F.Jonathan Ferrera: The ice was not as smooth as I was hoping (it was almost zamboni time anyway), but I had a great time nevertheless. It's perfect for people-watching.

Ian A.Ian Arsenault: The ribbon is 1/4 mile long and has a 2% grade. Admission is free. Skate rental is $12. Lockers are $1 via assigned magnetic key card. All lockers are approximately 1 cubic foot.

Patrick B.Patrick Buggy: Check the Zamboni times before you get there; it takes 30-60 minutes for them to run it, so you'll have to wait around.