Chicago 3-Day Itinerary

The perfect long weekend in Chicago: 3 days and 2 nights for about $1,234 for two, flights from New York included.

Three days of must-see attractions, local favorites, and insider tips, with what the weekend costs from where you fly.

Flying from

What 3 days, 2 nights costs

The fare from where you fly, two nights at the typical hotel night and three days of spend. Change it to fit your trip.

Travellers2

Nights2

Travel style

Changes daily spend only; the hotel night stays the same.

Fare · New York to Chicago × 2
Economy round trip, usually about $300 each
$600
Hotel night · $152 × 2 nights
What a night here usually costs, from hotel prices we check every week. 2 travellers share a room.
$304
Daily spend · $55 × 2 travellers × 3 days
Restaurants, transport and paid sights, per person per day. The hotel isn't in it.
$330

Trip cost: flights + hotel + daily spend$1,234

3 days, 2 nights, 2 travellers, mid-range, flying from New York. Usual prices we track ourselves, not a price you can book.

How we know

Fare: the middle price of the economy round trips we found from New York on our latest check (half were cheaper, half dearer), for departures in the coming weeks.
Hotel night: the middle nightly price of the Chicago hotels we check three times a week (see our hotel price index).
Daily spend: food, local transport and sights per person, from our city guide, by travel style. The hotel isn't in it.
Total: fare × travellers + hotel night × nights × rooms + daily spend × travellers × days. Prices move, so treat it as a guide, not a quote.

Each day's highlights in order. Want more days or a different pace? The planner at the end reshapes it around you.

1
Day 1Millennium Park
1. Chicago Riverwalk architecture tour
2. deep-dish at Lou Malnati's
2
Day 2Art Institute of Chicago
1. Michigan Avenue
2. Navy Pier at sunset
3
Day 3Field Museum
1. Museum of Science and Industry
2. Hyde Park
3. blues club on Halsted

Verified spots in Chicago that the classic route skips.

Hidden GemsMargie's Candies
A quirky, unchanged ice cream parlor open since 1921 in Bucktown that serves legendary hot fudge sundaes in giant clamshell dishes.
Hidden GemsGraceland Cemetery
This 19th-century cemetery on the North Side doubles as an open-air architecture museum, sheltering mausoleums designed by Louis Sullivan, Daniel Burnham, and other giants of American design.
Hidden GemsPalmisano (Henry) Park
A former quarry and landfill transformed into a surprising hilltop park in Bridgeport with panoramic skyline views virtually unknown to tourists.
Hidden GemsNational Hellenic Museum
A small but beautifully curated Greektown museum celebrating Greek-American history with rotating exhibitions and a striking modern building.
Hidden GemsThe Brimming Basket, LLC
A cozy neighborhood market and café in Logan Square beloved by locals for its thoughtfully curated pantry goods, freshly made sandwiches, and genuinely unhurried atmosphere far from tourist crowds.
Hidden GemsLa Pasticceria
A tiny, family-run Italian pastry shop in Ravenswood where homemade cannoli, sfogliatelle, and espresso are dispensed with old-world warmth to a devoted neighborhood following.

Each place was checked on Google Maps: real address, right city, still open.

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