Randi with a love of Chicago


I've been lucky enough to call Chicago my home for the past few years. I'm really fortunate that my job at the Tribune gives me a well-detailed and unique perspective into this city and what it has to offer.

These are a few of my favorite places I've dined, shopped and visited in Chicago — and the lessons I've learned while doing so. I hope you love everything on this list just as much as I do!

As a disclaimer, this city offers so many amazing possibilities for dining and entertainment. I couldn't possibly take advantage of them all. I keep a Chicago bucket list of all the things I want to do. Feel free to reach out with your suggestions — I'd love to add them.


Just hover over a star to learn more about my favorite restaurants and attractions here in Chicago. If I've written about a certain place, you can click to open the post in a new window.



Other things to check out?

  • There is so much to do outside in Chicago when the weather is nice. There are amazing farmers markets located all across the city. I also love running and walking along Lakeshore Trail, and the Millennium Park Summer Film Series is loved by many.
  • The Chicago Food Truck Finder is a great way to keep tabs on the best food trucks in town, and Small Tabs is a great resource for finding nearby drink specials to check out. Groupon is based here in Chicago, so I always check it for promotions before I buy any tickets since there are a lot of really good offers out there.
  • Zomato is my favorite app for restaurant reviews, but I also get a lot of suggestions from Thrillist and Eater pieces.
  • Support your local news while you're here! (The Chicago Tribune is my favorite.) 😉

Lincoln Park. I love the cluster of adorable stores and restaurants right off the Armitage Brown Line stop. Hop off the train and grab a doughnut at Glazed and Infused before stopping into Art Effect, Paper Source and All She Wrote to look at the baubles and trinkets. Walk north to Homeslice, grab a spot on the back patio and enjoy a cold pizza-garnished bloody mary.

Uptown + Buena Park. Check out a book from the Uptown Public Library and walk east to Montrose Beach. Pack the grill, meet up with some friends and spend the afternoon laying out. Walk south to Montrose Harbor to see the boats sail in-and-out, or or walk north to Montrose Dog Beach to watch the puppies play. Head back west to grab a drink and some apps at Bar on Buena for some sunburn relief.

Old Town. Dine, laugh and drink. Grab dinner at the Old Town Pour House, peep a comedy show at Second City and then grab drinks at the VIG and O’Brien’s.

River North + Streeterville. Play downtown tourist for a day — I promise, even the locals indulge in the gimmicks every so often. Start your morning with a beautiful view of the city from the Hancock. Make your way south along Michigan Avenue to get in some shopping, grab a cheezborger at the Billy Goat Tavern and wander up and down the Riverwalk along the Chicago River. Afterward, head east to Navy Pier, pick up a Rainbow Cone and enjoy the rest of your night dancing along to free music at the beer garden.

Hyde Park. Pick something off Obama’s menu at Valois for breakfast (cash only!) and then grab a coffee before making the 15-minute walk to the Museum of Science and Industry. (A Chicago zip code will get you a discount on tickets at the automated ticket systems.) Walk —  or bike using Divvy  — over to Promontory Point to take in the view.

Chinatown. Start downtown and take the Chicago Water Taxi (warning: I've had poor experiences with scheduled wait times) south to Chinatown. Hop off at Ping Tom Park, and walk over to Wentworth and Cermak. Grab a pastry from Chiu Quon and a bubble tea from Joy Yee, and browse the shops before taking the water taxi — or the Red Line — back home.

Wicker Park. Hop off the Blue Line at Damen and explore away. Grab coffee at Wormhole and make your way through the maze of Myopic Books and Reckless Records. Grab lunch at Antique Taco, hit up some of the shops along Damen, finish with dinner at Piece, a cocktail at Violet Hour (it's worth the wait!) and end your night with some air hockey and beers at Emporium.