CHICAGO, AS THE LOCALS LIVE IT
No algorithms. No tourist traps. Chicagoans from the SHFM planning committee hand-picked the places they love and would recommend. This is the city, as insiders experience it.
Want to see the city with SHFM first? SHFM has organized exclusive Tuesday outings to explore Chicago together — see what's in store.
The Insiders' Chicago Itinerary
Bob Kloeckner's Chicago Picks
Stop 1: Millennium Park (5 minute walk from the Palmer House)
- Cloud Gate (“The Bean”)
- Crown Fountain
- Lurie Garden (fall colors in October)
Stop 2: Chicago Riverwalk + Architecture Views (10 minute walk north to Michigan Ave bridge → stairs down to Riverwalk)
- Stroll west along the river
- Take in iconic architecture (Wrigley Building, Tribune Tower, modern glass towers)
Optional Foodie stop:
- Tiny Tapp / City Winery Riverwalk (seasonal but often open in October)
- Grab a coffee and enjoy the river views
Stop 3: Michigan Ave (Magnificent Mile Preview)
- Walk back up to street level and go north briefly on Michigan Avenue
- Pop into:
- Tribune Tower lobby (embedded world landmarks in walls)
- Garrett Popcorn (classic Chicago snack — mix cheddar + caramel)
Stop 4: Lets Eat Lunch in Style: Beatnik On The River (~8 minute walk west from Michigan Ave)
Stunning river views (right on the Chicago River) and it's a unique, upscale bohemian atmosphere (feels experiential, not just a meal). High-quality, shareable Mediterranean menu. Can't miss the Mezze spreads + grilled skewers and cocktails or rosé.
Davin Wickstrom's Chicago Picks
Stop 1: Coffee + Riverwalk Walk
- Begin the day where Chicago feels both calm and iconic: Walk the Chicago Riverwalk. A 1.25-mile, pedestrian-friendly path through the heart of downtown with skyline views and waterfront energy. This is not just a walk—it’s the best version of Chicago: architecture, water, movement, and space to think.
- Public Art & Architecture - Chicago is an open-air architecture museum. Walk it, photograph it, let it surprise you.
- First Lady - Explore Chicago’s iconic architecture or sightsee from the water.
Stop 2: Explore with Intention
- River North / West Loop: Design-forward streets, top restaurants and creative energy
- Wicker Park: Indie culture, boutique shops, and emerging creative scene
Stop 3 Lunch: Iconic + Local
- Robert’s Pizza and Dough Company: Waterfront-adjacent, high-energy setting with elevated pizza
- Manny’s Cafeteria & Delicatessen: Classic Chicago institution with deep local roots
Wednesday, October 7 — The Evening is Yours
Our planning committee carved out the evening of Wednesday, October 7 intentionally — so you'd have the time to actually experience dinner in Chicago. And, they know where to go, and they're not keeping it to themselves. After dinner, join SHFM for a night cap.
- Bavette’s Bar & Boeuf – Sexy, dimly lit, delicious steak house with a French flair. No notes.
- Rosebud on Rush – Don’t judge it just because it’s a chain…that’s because it’s so good it had to be repeated. Classic Italian, big portions, great atmosphere.
- Wilde Irish Bar & Restaurant – Go get a feel for the Lakeview neighborhood a short drive up Lake Shore…make sure and have the mac and cheese – best ever.
- Gibsons Bar & Steakhouse – A Chicago dining icon known for its legendary USDA Prime steaks, classic cocktails, and lively atmosphere that delivers the quintessential Chicago steakhouse experience.
- Gibsons Italia – A modern riverfront destination offering handcrafted Italian cuisine, premium steaks and some of the most spectacular skyline views in Chicago.
- Pequod’s – A Chicago favorite known for its legendary caramelized cheese crust and hearty pan-style pizza, making it a must-visit spot for the authentic Chicago pizza experience.
- Smyth – Chicago’s acclaimed three-Michelin-star restaurant, offering an inventive farm-to-table tasting menu that recently earned the title of Best Restaurant in North America by North America’s 50 Best Restaurants 2026.
- RJ Grunts (Lincoln Park) – The first salad bar ever in the US. This is also the first Lettuce Entertain You Restaurant.
- Chicago Pizza and Oven Grinders – A Chicago institution known for their “upside down pizza”.
- Bistro Monadnock – Great French food and not far from where we are staying.
- MCCB – Amazing Szechuan in Chinatown. It has been on the Michelin guide in the past.
- Duck Duck Goat – Chinese restaurant by Stephanie Izard. More affordable and easier to get into than Girl and the Goat.
- Bar Tutto - Offers Italian café fare that’s unpretentious and simply fantastic; it’s actually the sister restaurant to Rosemary, so both places have a warm connection and a welcoming vibe.
- Crying Tiger - A collaboration between Thai Dang and Lettuce Entertain You - Thai Dang is a well-known Vietnamese chef (he also owns Haisous), and this spot features creative Asian dishes with great energy, plus there’s a fun bar tucked away in the basement.
- Maxwells Trading - Stellar Asian fusion restaurant with strong Korean influences, thanks to its Korean chef, and it has earned plenty of nods and awards for its bold flavors.
- Momotaro - A Boka restaurant offering amazing Japanese cuisine and sushi - some of the best in the city, with a cool vibe and a fun izakaya in the basement where you’ll find inventive Japanese bar bites and creative drinks.
- Monteverde - An Italian staple in the city, serving up exceptional Italian food courtesy of a Top Chef chef.
- Rosemary - Sister to Bar Tutto, blending Croatian and Italian cuisine with a lively atmosphere and consistently great food.
- Avli on the Park – Fresh, Greek, and great service
- Beatnik on the River – Riverfront, Fusion, and Fun
- Gene & Georgetti – Chicago’s Oldest Steakhouse- Nostalgic old school Chicago
- Olio e Piu – Crisp fresh Italian Flavors
- Aba – Mediterranean and California flair, standout cuisine with sharable plates in a lush rooftop setting
- Lil Ba-Ba-Reeba – Fun, social, setting with sharable tapas perfect for lively group dinners
- Tre Dita – Tuscan-inspired Italian, handmade pasta, polished dining experience with best-in-class views of the city
- Ciccio Mio– River North, classic Italian, maximal design
- Handlebar – Wicker Park, small groups, patio, good for: pescatarian, vegetarian/vegan, gf, but don't let that scare you. This is my favorite restaurant in Chicago and is approved of by carnivores & veg-heads alike.
- Lao Peng You– Ukrainian Village, no reservations/can be hard to get into, but if you're considering getting takeout, this should be on your list.
- Matilda Restaurant– River North, Mexican & Peruvian, be sure to check out their speakeasy Clandestino
- Tryzub Ukrainian Kitchen – Ukrainian Village, patio, good for a group, highly recommend: the house-infused vodka flight – it's served on a Ferris wheel (get the horseradish, thank me later)
- Boka – Upscale, modern, refined
- Hiro Izakaya – Trend-forward, energetic, perfect for social dining
- Virtue Restaurant – Deeply respected, culturally rich, elevated Southern cuisine