Luxury things to do in Chicago
Merchandise Mart, Kyoten omakase, Smyth tasting menu, Alinea, Le Mistral
Two tasting-menu dinners, an omakase counter, and a city that rewards people willing to spend seriously on food. The days are paced deliberately so you arrive at each table hungry and present rather than rushed. This guide is for one kind of traveller only: the one for whom the meal is the trip.
Day 1: West Loop, Fulton Market
A polished coffee, a surprising outsider art museum, Monteverde's pasta at lunch, a browse at the Merchandise Mart, then dinner at Smyth's counter and nightcaps at After Chicago.
- 9:30 AM
- 10:30 AM
Intuit: The Center for Intuitive and Outsider Art
Small, singular museum for outsider and intuitive art, a genuinely unexpected cultural gem steps from Fulton Market.
Map - 12:30 PM
Monteverde
Acclaimed Monteverde is one of Chicago's most celebrated lunch destinations, the pasta here is the city's most talked-about.
Map - 2:30 PM
Merchandise Mart
Art deco giant on the river; most showrooms are trade-only, so stick to the ground floor and the riverfront.
Map - 7:30 PM
Smyth
John Shields' tasting menu built around a partner farm; ask for the counter seats facing the kitchen.
Map - 10:00 PM
After Chicago
After Chicago is the grandest cocktail bar in Fulton Market, the perfect high-end nightcap right around the corner from Smyth.
Map
Day 2: Logan Square and Omakase
A neighbourhood specialty roaster and a Doric column landmark set an easy morning tone before Lula Cafe's storied great-value lunch, a scenic walk on the Bloomingdale Trail, and an acclaimed omakase splurge at Kyoten Next Door with elevated cocktails at Best Intentions to close.
- 9:30 AM
Gaslight Coffee Roasters
Neighbourhood specialty roaster, solid single-origins to kick off the day.
Map - 10:15 AM
Illinois Centennial Monument
Iconic Logan Square landmark steps from the coffee shop, a grand Doric column worth a look before lunch.
Map - 12:30 PM
Lula Cafe
Lula Cafe is a Chicago institution, great value, beloved by every trusted guide, and the city's most storied neighbourhood lunch.
Map - 2:30 PM
Bloomingdale Trail Park
The elevated Bloomingdale Trail cuts through the neighbourhood, a scenic post-lunch walk without straying far.
Map - 7:30 PM
Kyoten Next Door
Otto Phan's omakase counter beside Kyōten; aged fish and seasoned rice, one piece at a time.
Map - 9:30 PM
Best Intentions
Logan Square cocktail bar that's serious about the drinks and easy about everything else.
Map
Day 3: Lincoln Park, the Big Finish
A Lakeview roaster, the Peggy Notebaert by the lagoon, Pequod's pan pizza for lunch, a browse at The Xchange, then Alinea and a glass at Le Mistral.
- 9:30 AM
- 10:15 AM
The Peggy Notebaert Nature Museum
Stunning nature museum on the lagoon, grand architecture and hands-on exhibits, a leisurely morning culture stop.
Map - 12:30 PM
Pequod's Pizza
Pan pizza with a caramelized cheese crust; a small, casual lunch before tonight's tasting menu.
Map - 2:30 PM
The Xchange
Critic-approved The Xchange, the luxury flagship shop pick to browse after lunch, just minutes away.
Map - 7:30 PM
Alinea
Grant Achatz's theatrical tasting menu; choose the Gallery or the Salon and leave the evening open.
Map - 9:30 PM
Where to stay
The Drake
The Drake is old Chicago grandeur done properly: Gold Coast address, landmark bar, and a short ride to every stop on this itinerary.
Nobu Chicago
Nobu Hotel sits in the West Loop near Smyth and After, with a rooftop pool and serious service.
Make Chicago your trip
Swearby drafts the days from places people swear by. Swap any stop, then invite the crew by text, even friends without the app. Vote on dates, track costs as you go, and everyone gets one number at the end.
Get Swearby on the App StoreBefore you go
Book ahead
- Chicago Architecture Center River Cruise aboard First Lady: a few days ahead
- Art Institute of Chicago: a few days ahead
- Wrigley Field: a few days ahead
- The Second City: a few days ahead
- Kingston Mines: a few days ahead
- Heli Chicago: weeks ahead
Skip these
- Navy Pier, a long pier of chain food and souvenir markup. Go only for the wheel view or the summer fireworks from the lakefront.
- Giordano's or Uno as the pizza pilgrimage. Pequod's is the local pick and Lou Malnati's the classic deep dish alternative.
- Doing both observation decks, especially in rain or fog. Pick one deck on a clear day or spend the money on the river cruise.
- Magnificent Mile chain shopping at flagship prices, and eating deep dish more than once. Once, shared and sit down, is the experience.
The full Chicago travel guide: when to go, safety, getting around