Things to do in Chicago
West Loop to Logan Square: locals' Chicago, one great dinner per night
This is a trip for someone who wants to eat and drink the way Chicago actually does: no tourist shortcuts, no spending more than necessary, one properly considered dinner each evening. Each day drops you into a different neighbourhood and lets it breathe, with an elevated rail trail, a blues basement, and a wood-fired dining room you'll be thinking about on the flight home.
Day 1: West Loop: deli, art, fire
Start with serious coffee at Sawada, spend an hour genuinely surprised by outsider art at Intuit, eat half a deli sub at Graziano's, and end the night at Rose Mary's wood-fired table before a pint at the Billy Goat.
- 9:30 AM
Sawada Coffee
Hiroshi Sawada's West Loop coffee bar; order the Military Latte, made with matcha and espresso.
Map - 10:30 AM
Intuit: The Center for Intuitive and Outsider Art
Small, free outsider-art museum just north of here, genuinely surprising and uncrowded.
Map - 12:30 PM
J.P. Graziano Grocery
Legendary Fulton Market deli, grab a loaded Italian sub, exactly the casual, value lunch this neighbourhood does best.
Map - 2:00 PM
Union Park
Union Park is a relaxed green patch, good post-lunch walk and a genuine neighbourhood hang.
Map - 7:30 PM
Rose Mary
Rose Mary's acclaimed Croatian-inspired cooking is the one memorable dinner this neighbourhood deserves, wood-fired and sharing-style.
Map - 9:30 PM
Billy Goat Tavern & Grill
West Loop outpost of the old newspapermen's tavern; a cheezborger and a cold beer.
Map
Day 2: Lincoln Park: deep dish and blues
Coffee in Lakeview, a walk past the Biograph, Pequod's caramelised crust at lunch, a clever and affordable Mexican dinner at Chilam Balam, then straight to Kingston Mines for as many sets as you can last.
- 9:30 AM
Coffee Lab & Roasters
Lakeview café that roasts its beans in the shop on Lincoln Avenue; good matcha too, and room to sit.
Map - 10:15 AM
Biograph Theatre
The 1914 theatre where FBI agents shot John Dillinger in 1934; a quick look from the sidewalk.
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 - 2:15 PM
Oz Park
Lincoln Park green with statues of Dorothy, the Tin Man, the Scarecrow and the Cowardly Lion.
Map - 7:30 PM
Chilam Balam
Great-value Mexican, inventive, shareable, and the one $$$ dinner that punches way above its price.
Map - 9:15 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: trail, tacos, cocktails
Gaslight gets the morning going, the 606 trail threads you through the neighbourhood on foot or bike, Chubby Boys handles lunch, and the evening runs from Mi Tocaya to La Licor Panamericana two blocks away.
- 9:30 AM
Gaslight Coffee Roasters
Local Logan Square roaster, solid morning coffee before hitting the trail.
Map - 10:15 AM
The 606
Walk or bike the elevated 606 rail trail, locals swear by it, threads right through Logan Square and Humboldt Park.
Map - 12:30 PM
Chubby Boys
Small Logan Square counter on Fullerton for a cheap, filling lunch before the trail.
Map - 2:30 PM
Illinois Centennial Monument
Illinois Centennial Monument is a striking Logan Square landmark, quick cultural stop worth the look.
Map - 7:30 PM
Mi Tocaya Antojería
Diana Dávila's Logan Square spot for regional Mexican plates to share, some you won't see elsewhere.
Map - 9:15 PM
La Licor Panamericana
Logan Square cocktail bar steps from dinner, with a Latin American bent to the drinks list.
Map
Where to stay
The Robey
The Robey sits in Wicker Park, a short ride to Logan Square and the West Loop, with a rooftop bar.
The Hotel at Midtown
The Hotel at Midtown splits the difference between Logan Square and Wicker Park, close enough to all three days without overcorrecting toward any one of them.
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