Chicago, USA 2 Day Itinerary

Day 1: Exploring Downtown Chicago

Only two CTA lines run all night, every night, the Red and the Blue. Everything else stops sometime after midnight and starts back up before 5am, so if your flight into O’Hare lands late, the Blue Line is your guaranteed ride into the Loop, about 45 minutes for $2.75 on a Ventra card, no matter the hour.

Morning: Start with breakfast at Amy’s Cafe & Bookstore in Wicker Park, a low-key neighborhood spot that beats a hotel buffet for the same money. Take the Blue or Brown Line downtown rather than driving. Parking in the Loop runs 30 to 50 dollars a day at most garages, which makes transit the obvious call even for a short trip.

Get to Millennium Park and Cloud Gate, the polished steel sculpture everyone calls The Bean, before 9am if you want a photo without forty strangers in the reflection. The crowd never really thins out after that, it just becomes part of the scene, so early is the only real trick. Admission is free and it is open dawn to dusk year round. From there walk to the Art Institute of Chicago, one of the oldest major art museums in the country, and worth setting aside at least two hours, not the twenty minutes people budget when they are trying to cram in too much.

Afternoon: Lunch at Girl and the Goat if you booked ahead. Reservations here go fast, often weeks out for prime dinner slots, so if you did not plan ahead, aim for a weekday lunch seating instead where walk-ins have better odds. After that, walk the Magnificent Mile on Michigan Avenue for the shopping and the Wrigley Building’s lit-up terra cotta facade, then continue to Navy Pier for the lake views and the Centennial Wheel. Navy Pier is more carnival than culture, so treat it as a twenty-minute stroll rather than the afternoon’s main event.

Evening: Dinner at Gibsons Bar and Steakhouse for a classic Chicago steakhouse night, then catch a show at Second City, the improv theater that gave the world Tina Fey, Stephen Colbert and Steve Carell before any of them were famous. Book the mainstage show over the smaller touring companies if this is your only night, it is consistently the sharper material.

Day 2: Discovering Chicago’s Neighborhoods

Morning: Breakfast at Ann Sather’s in Lakeview, known for cinnamon rolls the size of a fist, then take the Red Line down to Hyde Park for the Museum of Science and Industry. It is one of the largest science museums in the country and genuinely built for a half-day, not a quick pass-through, especially if the U-505 submarine exhibit is on your list.

Afternoon: Lunch at The Promontory, a restaurant and music venue in Hyde Park that doubles as one of the better rooms in the city for weekend live jazz. Take the Green Line back downtown and spend the rest of the afternoon in Wicker Park, browsing the independent shops along Milwaukee Avenue. This neighborhood has more personality per block than the Mag Mile, and it is the better call if you only have time for one shopping stretch.

Evening: Dinner at Avec for Mediterranean-leaning small plates and a wine list that punches above the room’s size, then decide between the two big observation decks. Skydeck at Willis Tower sits higher, at 1,353 feet, and throws in The Ledge, the glass balconies that jut out over the street, as part of general admission. 360 Chicago at the old Hancock building is shorter, cheaper, and less crowded, and it is the better pick if what you actually want in your photos is the skyline itself, since you cannot photograph Willis Tower’s silhouette from inside Willis Tower. Its own glass-floor feature, TILT, costs an extra 8 to 10 dollars at the desk and is not bundled into general admission the way The Ledge is.

Things to Know: The weather swings hard and fast off the lake, so pack layers regardless of season and check the forecast the morning of, not the night before.

Reservations matter more here than in most US cities. Girl and the Goat, Avec and the better steakhouses all book out days or weeks ahead for prime times.

On the deep dish debate, Lou Malnati’s is the more affordable, broadly reliable choice, while Pequod’s caramelized, crispy-edged crust is the one locals argue is actually better. Either way, one deep dish meal is plenty for a two day trip. It is dense enough to skip a second sitting.

Transportation: The CTA covers the city well, but only the Red and Blue lines run 24 hours. Confirm your last-train time before a late night out, or budget for an Uber or Lyft back, both of which operate normally throughout the city.

Tips: A Go City or CityPASS bundle can pay for itself fast if you are hitting three or more paid attractions like the Skydeck, the Art Institute and the Museum of Science and Industry. Do the math against buying tickets separately before assuming it is a discount, since not every attraction on the pass is one you will actually use in two days.