Google completes "first time in chicago" with "what to do", "where to stay", "itinerary", "must do" and "reddit". Here are all of them, from someone who lives here.
Where to stay#
The Loop and River North for a first visit (the L, the river, the architecture, the Bean); the West Loop for restaurants; Lakeview and Lincoln Park for neighbourhood life and Wrigley; Wicker Park and Logan Square for bars and a younger crowd; Hyde Park for the university and quiet.
What to do#
- The architecture river cruise: the single best thing to do in the city, and the first.
- The Art Institute and Millennium Park on the same afternoon.
- The Lakefront Trail and a beach (North Avenue, Oak Street, Montrose).
- A neighbourhood on foot: Pilsen, Logan Square, Andersonville, Hyde Park.
- Deep dish once, then the real Chicago food: tavern-style thin crust, Italian beef, a Maxwell Street Polish, Pilsen's taquerias, Devon Avenue, Chinatown, Argyle Street.
- A game: Wrigley in summer, the United Center in winter.
- Comedy at Second City or iO.
- Summer: a street festival (there is one every weekend) and the free concerts at the Pritzker Pavilion.
What to skip#
Navy Pier beyond the Ferris wheel, the Magnificent Mile as a destination, and a trip that never leaves downtown.
Getting around#
Yes, completely. Stay in the Loop, River North, the West Loop or Lakeview; the L from O'Hare (Blue line) and Midway (Orange line) runs straight downtown; the Lakefront Trail and the river walk are on foot; Divvy bikes cover the gaps. The only things that need a car are the suburbs and the far South Side. Chicago without a car has the detail.
A three-day itinerary#
Day one, downtown: the river cruise, the Art Institute, Millennium Park, dinner in the West Loop. Day two, the North Side: the Lakefront Trail, Lincoln Park and the free zoo, Wrigleyville or Lakeview, comedy at night. Day three, the neighbourhoods: Pilsen morning, Hyde Park afternoon (the Robie House, the Point), blues on Halsted at night.
The mistakes everyone makes#
Coming in January without a real coat; never leaving the Loop; deep dish twice; underestimating the distances on the lakefront; skipping the neighbourhoods, which are the city.
Or a local, for an afternoon#
On Roavi you can hire a Local Friend, someone from Chicago, for a few hours at a rate they set (most list $15 to $50), platonic and in public: the food neighbourhoods with someone who grew up on them, a game with a fan, the version of the city that is not in this itinerary. Roavi lists no Local Friends in Chicago yet, which is the honest number and the reason the first people to list here will get every message; messaging is free for the people who write to you. Rent a friend in Chicago.
One afternoon with someone who lives here.
Meet local guides in ChicagoFrequently Asked Questions
Where should I stay in Chicago for the first time?
The Loop and River North for a first visit (the L, the river, the architecture, the Bean); the West Loop for restaurants; Lakeview and Lincoln Park for neighbourhood life and Wrigley; Wicker Park and Logan Square for bars and a younger crowd; Hyde Park for the university and quiet.What should I do on my first time in Chicago?
The architecture river cruise: the single best thing to do in the city, and the first. The Art Institute and Millennium Park on the same afternoon. The Lakefront Trail and a beach (North Avenue, Oak Street, Montrose). A neighbourhood on foot: Pilsen, Logan Square, Andersonville, Hyde Park.Do I need a car for a first trip to Chicago?
Yes, completely.