[updated June 2020]
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.
- Guide to Biking in Chicago
- 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
The Selfie Stick: A Traveler’s Best Friend
I’m in the UK and have booked to visit Chicago in November for http://www.therugbyweekend.com so will spend some time going through all your info to put together a list of things to see, do, eat and drink (when not at the rugby!)
Hi Mike! Thanks for commenting. Wow, that’s so cool. I hadn’t even heard of that yet. Good to know it’s coming. I HOPE it’s still warmish when you come in November. There’s TONS to see and do here..so it all depends on your interests. If the weather is warm, definitely hang out/bike/play on the Lakefront. And enjoy all the neighborhoods.
Wow, great guide Lisa! Being a Chicago-native I found this very useful. For any locals or visitors that are traveling on a budget there are great Free Chicago Walking Tours (http://www.freechicagowalkingtours.com) available in the city as well. The tours give guests an opportunity to experience Chicago with a local guide regardless of their budget. Great to get some exercise, learn the history and plenty of opportunities to take pictures of Chicago’s most iconic sites.
Good writeup, Lisa. Definitely something I can show to visitors who come through. I’ve been here for 8 years and *still* haven’t discovered everything that the city has to offer. It’s impossible to keep up with all the food. But I hear Duck Duck Goat is the bomb.
Hey Dan! Thanks for your comment. I am constantly discovering more about Chicago and I’ve lived here 18 years! I haven’t been to Duck Duck Goat yet, but have done Girl and the Goat. 🙂 Where did you move here from?
I grew up in the Virginia mountains. It’s a pretty place, but I got bored and wanted to live somewhere with more going on. I decided between Chicago and New York, and didn’t have the patience for New York.
Now I make my base in Chicago and travel, kind of like you. I’m coming back in 3 weeks, and I bet there’s like 4 new places to eat. 🙂 Are you out traveling now, or chilling in the city?