103 reasons to plan a Chicago vacation (and wander the city by bike)

 Dearborn is part of Emanuels's vision to install 645 miles of cycle track. 

Dearborn is part of Emanuels's vision to install 645 miles of cycle track. 

 Best eats, drinks, sights by bike in Chicago on Pinterest

Best eats, drinks, sights by bike in Chicago on Pinterest

100 miles of existing cycle tracks (545 in the future)

+ 1 scenic Lake Front path extending 18 miles along the Lake Michigan shoreline

+ Divvy bike share

+ Neighborhoods full of local restaurants, craft beer, parks, shops and more

= a damn pleasurable way to wander Chicago by bike

With Bloomberg no longer at the helm in New York City, Chicago Mayor Rahm Emanuel has taken over the national spotlight as the most bike-progressive mayor of a major American city. And while the biking experience is not yet up to the level of the world's best biking cities, it is getting closer by the month due to Chicago's aggressive goals. Make no mistake, bike infrastructure goals matter. Chicago has pledged to have 645 total miles of cycle tracks, with roughly the first 100 miles of it done by Fall of 2014. Neighborhood greenways continue to expand throughout Chicago, and they will add at least 175 more Divvy bike share stations to expand and strengthen the bike sharing network. A "Lakefront Flyover" pedestrian and bike bridge is in the planning stage, which will carry people safely over several current street crossing pinch points in elegant fashion. Another goal the city is aggressively pursuing is to add at least 800 new parks, with the 606 serving as Rahm Emanuel's signature project, in which a dis-used rail line will be turned into much-needed green space in the northwestern part of Chicago that needed it most.

Add to all these bold plans the fact that Chicago is laid out on a grid, that 8 different "kiddical mass" rides happen in different neighborhoods each month, that it has over 18 miles of Lakefront Path gloriousness, and that Chicago is the only city whose Transportation Commissioner (Rebekah Scheinfeld) agreed to meet us while we were in town, and Chicago is already a compelling place to see by bike. And it will only get better.

City Guide

Chicago trip planning resource includes tips on bike rentals, lodging, transportation and biking 101

Routes

Best Eats, Drinks & Sights by Bike

Eats

 Big Star has delicious tacos and tequila drinks.  During the summer, get there early, because the patio fills up quickly. 

Big Star has delicious tacos and tequila drinks.  During the summer, get there early, because the patio fills up quickly. 

  • Handlebar Restaurant - vegetarian restaurant with "back yard style" patio and owners that bike
  • Karyn's On Green - pricier, but very tasty vegetarian restaurant with minimalist interior
  • Calumet Fisheries - best seafood, most unassuming joint in town at the southern edge of the Lakefront Path
  • Honky Tonk - best BBQ
  • Little Goat - brunch hotspot with attached general store and roof top patio that commands the best happy hour view in Chicago
  • Orange - founder's long time favorite brunch spot with GF pancakes, fruit sushi and made to order juice.  multiple locations
 Heritage General Store is both coffee shop and beautiful bike shop with nice accessories. 

Heritage General Store is both coffee shop and beautiful bike shop with nice accessories. 

Drinks

  • Sportsman's Club - known for beer and townie decor complete with checker game tables and wooden checkers
  • Wormhole Coffee - 2015 must be this coffee joint's year. You won't miss the DeLorean
  • Big Star Tacos - tasty tequila drinks, unique tacos and huge outdoor patio in the heart of Wicker Park
  • Haymarket - Greektown beer bar with decent food and vintage track parked out front to drool over
 Field museum is expensive but it's situated on the Museum Campus, a scenic biking destination. 

Field museum is expensive but it's situated on the Museum Campus, a scenic biking destination. 

Shopping

  • BFF Bikes - shop run by 2 kick ass ladies carries girly bikes and accessories
  • Heritage General Store - part coffee shop, part boutique bike shop with Brooks accessories and other transportation biking accessories.  They even have their own parklet out front

Sights

  • Chicago Architectural Tour - so many buildings, so little time, so let the professionals do it for you.  Plus, it's on a boat.
  • Field Museum - expensive admission at $31, but they represent over 4.6 billion years of history and in the least, it's location in Museum Campus is a scenic biking destination

Parks

  • Oz - tin man statue! 
  • Mary Bartelme Playground - this is one of the founders' daughter's favorite playgrounds because of the Indiana Jones style obstacle course. Also features a really nice dog park
  • Northerly Island - commands the best views of the city, yet helps you escape the hustle with 180 views of Lake Michigan.
  • Millenium's Maggie Daley Playground - Just opened December 2014 and features an ice skating "ribbon" in the winter and what looks like a play-n-spray on steroids in the summer