Tre Dita
Tuscan Steakhouse • The St. Regis Chicago
Chicago's newest must-visit Italian restaurant has arrived. Chef Evan Funke—the two-time James Beard-nominated pasta master behind LA's Felix and Mother Wolf—has partnered with Lettuce Entertain You to bring authentic Tuscan cuisine to the stunning St. Regis Chicago. The name "Tre Dita" (three fingers) refers to the precise thickness of a properly cut Bistecca Fiorentina, and everything here is executed with that same obsessive attention to detail.
The star attraction is the temperature and humidity-controlled "Pasta Lab" where chefs hand-roll, cut, and shape pasta in full view of diners. The Cacio e Pepe and Rigatoncini All'Arrabbiata are standouts—thick strands coated in rich cheese sauce with enough pepper to give each bite serious zip. But don't sleep on the proteins from the open-hearth wood-fired grill or the 700+ bottle all-Italian wine list.
Location
401 E Wacker Dr, 2nd Floor
The St. Regis Chicago
Hours
Sun–Thu: 4–10pm
Fri–Sat: 4–11pm
Reservations
Via OpenTable
14 days in advance
Adam & Timothy's Tip
Reservations drop at midnight, 14 days out—set an alarm if you want prime Saturday times. Can't get in? Bar Tre Dita is first-come-first-serve and serves the greatest pasta hits. The 40-foot windows offer some of the most stunning views in the city, especially at sunset. This is certified as the first authentic Tuscan restaurant in the United States by Vetrina Toscana.
Fine Dining
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New & Noteworthy 2025–2026
We left Chicago several years ago, so we can't personally vouch for all of these—but we've done the research and summarized what the critics and locals are saying. One thing we know for sure: Chicago restaurants don't last long if they're not good.
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Lao Cuisine
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Neo-Bistro
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Roman Italian
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Ultra-Luxe Steakhouse
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Midwestern Hearth
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Peruvian-Japanese
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Book Your Table
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Hotel Bars
Top Things to Do in Chicago
Beyond the restaurants—our picks for experiencing the best of the city.
The Art Institute of Chicago
One of the world's great museums. Period. We never tire of it. The Impressionist collection alone is worth the trip, but don't sleep on the modern wing or the Thorne Miniature Rooms. Plan for at least half a day—you'll want it.
Millennium Park & The Bean
Yes, it's touristy. Yes, you should still go. Cloud Gate is genuinely impressive in person, and the park itself is beautifully designed. Hit it early morning to avoid the crowds, then grab coffee nearby.
Architecture River Cruise
The single best way to understand Chicago's architectural heritage. We've done this a dozen times and still learn something new. Go with the Chicago Architecture Center tour—the docents are exceptional. Spring through fall only.
Live Jazz & Blues
Chicago is a music city. Green Mill for jazz (Al Capone's old haunt), Kingston Mines or Buddy Guy's Legends for blues. These aren't tourist traps—they're living history. Go late, stay later.
360 Chicago or Skydeck
We slightly prefer 360 Chicago (formerly Hancock Observatory) for the views and the TILT experience. Skydeck's Ledge is iconic but expect longer lines. Either way, go at sunset if you can swing it.
Second City or Improv
The birthplace of modern improv comedy. Tina Fey, Steve Carell, Bill Murray—they all started here. The shows are consistently sharp and surprisingly affordable. A perfect post-dinner activity.
Walk the Lakefront Trail
18 miles of gorgeous waterfront. We love the stretch from Navy Pier down through Grant Park. Rent bikes if walking isn't your thing. On a clear day, this is Chicago at its absolute finest.
Catch a Game at Wrigley
Even if you're not a baseball fan, Wrigley Field is a bucket-list experience. The neighborhood, the rooftops, the seventh-inning stretch—it's pure Americana. Cubs or not, you'll feel the history.
Explore Neighborhood Shopping
Skip the Magnificent Mile chains. Instead, wander through Wicker Park for vintage and indie boutiques, or hit up Andersonville for antiques and local makers. The West Loop has excellent design shops too.
Rooftop Bar Hopping
Chicago does rooftops exceptionally well. Cindy's at the Chicago Athletic Association has killer views. London House is another favorite with stunning panoramas. Summer nights only—winters are brutal.
Explore Our Austin Guide
Austin is home now—and our guide there is far more extensive. We've already helped hundreds of people buy, sell, or lease in Austin and have built a real community. You'll find neighborhood guides with school and amenity information, trusted vendor referrals, restaurant recommendations, happy hour guides (because Austin food and drink prices are no joke!), plus cocktail and food recipes we love to make at home.
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