Chicago in 2, 3 or 4 Days: Can You Do It for US$200? One Plan, Grouped by Area

Three days: the default plan

One district a day, so you never cross the city twice: the Loop, the river, then the lakefront. Each day block has the times and tickets.

1. Day 1: the Loop. The Art Institute in the morning, Millennium Park and the Chicago Cultural Center at midday, the Skydeck at sunset.
2. Day 2: the river. The Riverwalk, an architecture cruise from the Michigan Avenue Bridge, then Michigan Avenue on foot.
3. Day 3: Museum Campus. The Field Museum, then the lakefront path with the skyline ahead of you.
4. Before you fly: book the Skydeck slot and the Art Institute guided visit, because a slot and a start time fix Day 1.
5. The day before: pick your cruise departure. Boats run on a seasonal calendar, so confirm they are sailing on your dates.
6. Day order: Tuesday suits Day 2, because the Art Institute is closed that day.

Day 1: The Loop, about US$120

The stops run from Michigan Avenue in the east to Willis Tower in the west, so the day never doubles back. Start with the paid museum visit while you are fresh and finish with the Skydeck at sunset.

See or book Skydeck tickets →

1. Start at the Art Institute. It opens to the public at 11am; book the guided skip-the-line visit, which includes entry and has its own start time.
2. Walk north into Millennium Park, free from 6am to 11pm, and stroll its gardens and lawns.
3. Walk on to the Chicago Cultural Center at 78 East Washington Street and look up at the Tiffany dome in Preston Bradley Hall.
4. Head west to Willis Tower for a Skydeck slot near sunset, and enter on Jackson Boulevard.
5. Arrive 15 minutes before your slot; most visits last 45 to 60 minutes.

Day 2: The river and Michigan Avenue, about US$45

The river is the spine of the day: walk it at water level, then see the towers from a boat. The Riverwalk and the cruise both run every day of the week, so this is the day to put on a Tuesday.

See or book an architecture river cruise →

1. Start on the Riverwalk, free from 6am to 11pm, a path of 1.25 miles along the river.
2. Board the architecture cruise at the Michigan Avenue Bridge; confirm the dock and departure time on your booking.
3. Walk north up Michigan Avenue, the Magnificent Mile, which runs from the bridge to Oak Street and passes the Water Tower.
4. Return to the Riverwalk after dark; it stays open until 11pm.

Day 3: Museum Campus, about US$35

Choose one building, because each fills a morning. The Field Museum is the anchor here and the lakefront path finishes the day. Two L rides and a short walk are all the transport you need.

See or book Field Museum tickets →

1. Ride the Red, Orange or Green Line to Roosevelt, then walk or take the 146 bus from State and Roosevelt to the campus.
2. Enter the Field Museum when it opens at 9am; on regular days last entry is 4pm.
3. Swap in the Shedd Aquarium or the Adler Planetarium next door if you prefer marine life or astronomy; each is a separate ticket.
4. Walk the lakefront path north from the campus for the skyline view, then ride back on the L or the 146 bus.

If you have two days

Keep the Loop day whole and fold the river and the lakefront into one day, cruise first and museum after.

1. Day 1: the Loop exactly as above, ending with the Skydeck at sunset.
2. Day 2: the river cruise in the morning, then the L to Roosevelt for the Field Museum from early afternoon; last entry is 4pm.
3. Drop the Magnificent Mile walk and the evening Riverwalk stroll; they are the cost of the cut.

If you have a fourth day

A fourth day is a list, not a route: choose one side of the city. Each side needs its own L ride, and a full day out of the city belongs to the day-trips guide.

Facts that shape the trip

Two closing days and one fare decide the order of the days. The matrix shows what is open when; the points cover fares and how ticket prices move.