Things to do in Chicago, splurging
Avec, Galit and Andros Taverna for dinner, Pequod's pan pizza, blues at Kingston Mines.
This is a Chicago trip built around the table: every evening lands at a destination restaurant, every afternoon has room to shop or breathe, and the nights end at bars where the drinks are actually worth ordering. It suits someone who will spend real money when the quality is there, and who wants a plan that holds together rather than a list of names to google.
Day 1: River North, the Loop, West Loop
Start with a tight espresso at Doma, work through an acclaimed lunch at Avec, take the Tiffany dome at the Cultural Center on your own terms, and finish with dinner at The Dearborn and inventive cocktails at MONEYGUN.
- 9:30 AM
Doma Cafe
Neighbourhood specialty café right in River North, a tight, well-edited espresso program to kick the day off.
Map - 12:30 PM
Avec
Cedar-lined West Loop room with a long communal table; order the chorizo-stuffed dates and the focaccia.
Map - 2:30 PM
Chicago Cultural Center
World's largest Tiffany glass dome in a free landmark building most visitors walk right past, genuinely spectacular interior.
Map - 4:30 PM
Maggie Daley Park
40-foot outdoor climbing wall with routes for all levels, quarter-mile Skating Ribbon for rollers and scooters.
Map - 7:30 PM
The Dearborn
Polished Loop tavern across from the theatres; a good burger or a full dinner before a show.
Map - 9:30 PM
MONEYGUN
MONEYGUN is the best craft-cocktail bar in the West Loop, inventive, punchy drinks steps from dinner.
Map
Day 2: Lincoln Park and the lakefront
A morning walk along North Avenue Beach, deep dish at Pequod's, a browse at The Xchange, then Galit for dinner and the blues at Kingston Mines.
- 9:30 AM
- 10:30 AM
North Avenue Beach
Chicago's see-and-be-seen lakefront beach, postcard skyline views, volleyball, and a morning stroll before the crowds arrive.
Map - 12:30 PM
Pequod's Pizza
Pan pizza with a caramelized cheese crust that blackens against the pan; a small one feeds two.
Map - 2:30 PM
The Xchange
Critic-picked boutique for design and curated finds, exactly the design-shop browse this traveller lives for.
Map - 7:30 PM
Galit
Middle Eastern cooking around a live-fire hearth; start with the hummus and pita straight from the oven.
Map - 9:30 PM
Kingston Mines
Two stages and blues every night until late; walk in, get a beer and stay for a few sets.
Map
Day 3: Logan Square, start to finish
Gaslight for the first espresso, The 606 on foot or bike, a long lunch at Lula Cafe, then Greek at Andros Taverna and cocktails at Best Intentions.
- 9:30 AM
- 10:30 AM
The 606
Elevated rail trail through Logan Square, walk or bike and drop down for neighborhood exploration.
Map - 12:30 PM
Lula Cafe
Logan Square's farm-to-table pioneer since 1999; the seasonal plates and pastas change constantly.
Map - 2:30 PM
Illinois Centennial Monument
Illinois Centennial Monument fixture Logan Square, a quick, iconic photo stop before heading to dinner.
Map - 7:30 PM
Andros Taverna
Greek taverna on Milwaukee Avenue; wood-grilled fish, spreads and a deep Greek wine list.
Map - 9:30 PM
Best Intentions
Logan Square cocktail bar that's serious about the drinks and easy about everything else.
Map
Where to stay
Waldorf Astoria Chicago
The top-tier address in the Gold Coast: close to Day 1 and Day 2 stops, and the level of finish matches what this trip is spending on dinner.
The Robey
The Robey puts you in Wicker Park, a short ride from Logan Square and easy to Fulton Market, with a rooftop and rooms that have actual design intent.
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