[updated September 2019]
I’ve lived in Chicago for more than 20 years now, and even when I was on the multi-year round-the-world trip that launched this blog, I thought of my home city often. For my 10 years as a TV producer at ABC7, it was my job to research, write and produce segments for broadcast on my adopted hometown. It’s one of the reasons I fell so hard for the city; I got to know so many people and so many great stories, neighborhoods, and restaurants! I’ve also written about it a lot for publications and on this blog. So, I decided to compile this ultimate Chicago guide and share with you everything that makes this city great!
Ultimate Chicago Guide
1. The City Itself
Chicagoans LOVE Chicago, and with good reason! Check out these posts if you’re skeptical of the city’s awesomeness and need an overview of why we love it here.
- Sharing My City
- I Heart Chicago
- Chicago — the City of Now
- I Have a Crush on… Chicago
- Told You So
- Falling in love all over again
2. The Lakefront and the Chicago River!
I dare you to spend some time walking along the Lakefront and not feel your spirits lift. Better yet, take a boat ride! Whether it’s on Lake Michigan or the Charles River, you’ll be treated to beautiful views of the city.
- Outdoor Activities in Chicago
- Come Sail Away on Chicago’s Lake Michigan
- Video: It’s Electric! A Boat Ride on the Chicago River
- 24 Hours on the Chicago River: My Night at the Museum
- Chicago Architecture Foundation River Cruise
4. The Food
You knew I was going to mention this, right?
- The Best Outdoor Dining in Chicago
- Ethnic Food Chicago
- Urban Farming in Chicago
- Foodseum: Chicago’s new Food Museum
- Chicago’s Green City Market
- Chicago Eats: The ULTIMATE Guide to the Best Restaurants in Chicago
- Chicago’s Best NON Deep Dish Pizza
- Eating Like a Rockstar at Chicago Gourmet
- A Mexican Food Tour through Pilsen
5. The Walk-ability and Bike-ability
You definitely don’t need a car to explore Chicago. I should know — I haven’t owned a care here in 8 years, and I’ve gotten by just fine with my trusty bike.
- The 606 and Bloomingdale Trail
- Bicycling in Chicago and Around the World
- Walk the Walk: The Most Pedestrian-Friendly Cities in the US
6. All the great neighborhoods to stroll through
Now that you know what a pedestrian-friendly city Chicago is, take a walk through one of my favorite neighborhoods with this series of photo essays:
- Chicago Block by Block: Kenwood and Obama’s Chicago Home
- Chicago Block by Block: Ravenswood Manor
- Chicago Southland
- Chicago’s Gold Coast
- Wrigleyville: Home of the Chicago Cubs… and Me
- Chicago Block-by-Block: Grace Street
- Chicago Block-by-Block: Astor Street
- Chicago Block-by-Block: Lakewood Balmoral District
- Chicago Block-by-Block: Rush Street
- Chicago Block-by-Block: Dearborn Parkway
7. There’s always something happening
Especially in the summer!
8. Plus, all the landmarks to see (and photograph!)
Between the second oldest baseball stadium in the country and the quirkily (is that a word?) iconic Superdawg, you’ll definitely see something worth photographing.
Check out this post from my friends over at the Local Tourist for a fabulous, comprehensive list of things to do in Chicago.
Check out these Chicago guides I’ve written for other sites and magazines
- Ethnic Chicago – Scandinavian Traveler
- A Local’s Chicago – West Jet Magazine
- Summer in Chicago – Jetsetter.com
- Choose Your Romance: Date Night in Chicago – Marriott Traveler
- Guide to Chicago’s Best ‘Hoods – Marriott Traveler
- Unique Stays in Chicago – Huffington Post
- Wrigley Turns 100 – American Airlines
- Eataly Chicago – American Airlines
- Chicago’s Latin Food Scene – The Latin Kitchen
- What to Do in Chicago – YTravel Blog
- Top 10 Places to Eat in Chicago – The Planet D