Kristen Klus, head concierge at Four Seasons Chicago, shares her favorite ways to enjoy the beautiful city of Chicago. Kristin has gathered the savviest sight-seeing suggestions she could find from not only her own experience, but other local connoisseurs. Discover the glittering city beside the lake, with its iconic architecture, art, sports, shopping and fine dining.
For the sports enthusiasts, Harry Caray’s and the Chicago Sports Museum are must-visit destinations, especially for any Boston sports fans. The Peggy Notebaert Nature Museum is one of many great museums perfect for sharing with the kids; the beautiful displays and amazing butterfly haven are a must see. The T-shirt Deli is the best place to pick up a unique and custom souvenir for yourself or for someone back at home. With so much to see and do, it’s no wonder families are flocking to Chicago for their next vacation.
Also read: The Best Luxury Hotels Of Chicago
Here are more of Kristen’s top picks for Chicago, courtesy of Four Seasons Chicago.:
Food, Drinks and Nightlife
Kristan’s favourite “must-try” local dish or drink you won’t find elsewhere: Deep-dish pizza! It’s not as over the top as you think.
Kristan’s favourite local celebrity chef: Rick Bayless and his restaurants Frontera Grill and Topolobampo. Xoco is also great for walk-up counter service.
Kristan’s favourite restaurant only locals know about: Riccardo Trattoria. You’d think you travelled to Italy—but the secret is getting out!
Kristan’s favourite place for pizza: Hmm … picking only one pizza joint is a tough decision! Our vote goes to Lou Malnatis, the original and best. Be sure to order the butter crust! This place is also a very kid friendly.
Kristan’s favourite place for a hot dog: The best hotdog is at the Hotel’s own Allium. Don’t take our word for it—it was voted No.1 by Time Out Chicago.
Kristan’s favourite place for a burger: For savoury burgers, go to Kuma’s Corner (there are lines there for a reason).
Kristan’s favourite place for vegetarian: The Chicago Diner in Boystown has been “meat free since ’83.” The Seitan “wings” are so good!
Kristan’s favourite place to dine al fresco: At Piccolo Sogno, you’ll feel as though you’ve left the city when sitting in its green garden terrace.
Kristan’s favourite coffee shop: Any Intelligentsia Coffee location, or coffee shop that sells it.
Kristan’s favourite place for brunch: The best brunch in Chicago is at Allium, of course. Try the PB&J French toast.
Kristan’s favourite food trend: Doughnuts are a new top trend! We love The Doughnut Vault and its get cake doughnut. For another sweet treat, try Sprinkles Cupcakes‘ classic vanilla cupcake.
Kristan’s favourite romantic restaurant: Les Nomades is very intimate and chic. Nothing is cosier than snuggling on one of their banquettes.
Kristan’s favourite kid-friendly, non-chain downtown restaurant: Quartino Ristorante & Wine Bar is a Chicago classic. Note that it can get a bit noisy!
Kristan’s favourite sushi restaurant: There are so many great sushi restaurants in Chicago to choose from, but my fave is Arami.
Kristan’s favourite rooftop patio: A great rooftop patio is the ROOF on the Wit. Its great view, drinks and Miami-chic vibe are perfect for summer!
Kristan’s favourite cocktail: That has to be Gilt Bar’s 20th Century cocktail. Stay for a while and go down to Curio, their speakeasy in the basement!
Kristan’s favourite drink trend: ʺHopʺ on the craft beer trend with the Chicago Beer Experience Beer Tour, a great way to try local brews.
Kristan’s favourite pick for a night on the town: Dinner at Chicago Cut Steakhouse followed by jazz at the Green Mill Jazz Club.
Kristan’s favourite spot for late-night eats: Au Cheval or Tempo Cafe—depends if you’re looking for gourmet or comfort food, respectively. Either one is a sure bet.
Kristan’s favourite wine list in the city: Chicago Cut Steakhouse has a great wine list, where you can order wine on an iPad.
Kristan’s favourite lounge: If you’re looking for a lounge atmosphere, head to The Violet Hour.
Kristan’s favourite pub: Try The Gage or Sheffield’s.
Kristan’s favourite itinerary for perfect night on the town: Dinner on the terrace at Chicago Cut, followed by taking in a blues set at Buddy Guy’s Legends.
Kristan’s favourite place to listen to live jazz: Definitely the legendary Green Mill Jazz Club. Be sure to catch singer Kimberly Gordon belt it out on Sunday nights.
Kristan’s favourite place to listen to live rock/alternative music: Head to the Empty Bottle to see great live music.
Kristan’s favourite place to dance the night away: Danny’s Tavern in Wicker Park.
Kristan’s favourite only-in-Chicago experience: That would be listening to jazz at the Green Mill Jazz Club, a former 1920s speakeasy that was once a hangout of Capone.
Kristan’s favourite photo ops in the city: The best place for photos is from aboard the deck of an architectural river cruise, just as you round the bend on the Chicago River.
Kristan’s favourite city view: The north steps of The Field Museum offer a perfect skyline view.
Kristan’s favourite Chicago hidden gem: The Driehaus Museum—you could walk right past it unless you’ve been clued in.
Kristan’s favourite must-do: Don’t leave Chicago without a show at The Second City! You’ll laugh until your sides hurt.
Kristan’s favourite thing that surprise visitors about Chicago: This city is home to more than 10 delicious cupcake shops.
Kristan’s favourite way to explore the city: Explore on foot, or by hopping from “L” to “L”. You feel the pulse of the city best this way.
Kristan’s favourite place for shopping: Go to Wicker Park or Bucktown—boutiques, vintage … it’s all there.
Kristan’s favourite boutiques: My fave local designer boutiques are Cynthia Rowley in Wicker Park and Eskell.
Kristan’s favourite place to buy souvenirs: The Chicago Architecture Foundation store on Michigan Avenue has some of the most original Chicago items out there.
Kristan’s favourite and most unique spa: Allyu Spa is right on the river. You’ll feel as though you’ve stepped into an ashram!
Kristan’s favourite neighbourhood for a stroll: Andersonville for its cosy cafes, cute shops—you’ll lose all track of time.
Kristan’s favourite place for people-watching: The best place is the Gold Coast neighbourhood. Grab an outdoor table at Gibsons Bar & Steakhouse and see a bit of all walks of life stroll by.
Kristan’s favourite day trip outside of the city: If you have time, head to Chicago Botanic Garden. It’s so lush and beautiful, you’ll think you’re in a tropical destination.
Kristan’s favourite weekend trip outside of the city: Galena, Ill. is a charming place just two-and-a-half hours north of the city. Step back in time on the town’s quaint Main Street with its kitschy shops.
Kristan’s favourite summer activity: In the summer, nothing beats a tour of Wrigley Field—but catching a game is even better!
Kristan’s favourite must-dos for first-timers: Take an architectural boat cruise and visit the Art Institute of Chicago.
Kristan’s favourite way to spend a rainy day: Exploring the Museum of Science and Industry. You could get lost in just about any of their amazing exhibits.
Kristan’s favourite museum/art gallery: The Art Institute of Chicago has the largest collection of Impressionist art outside of Paris! And it’s a must for fans of Ferris Bueller’s Day Off.
Kristan’s favourite running path: Lakefront Bike Path is great for runners, too. If you’re game, run past Irving Park and through the Peace Garden—it’s small, but so special.
