Downtown Chicago hotels now add about 19% in taxes and fees, and the Skydeck, an architecture cruise and the Art Institute each cost $30–55 a person. Airport taxis, hotel parking and tipping push most trips well past the plan.
Starts with a sample trip. Change any number to match yours.
Compare hotels in downtown Chicago →With flights, a downtown hotel and food, plan on about $1,850. Once you add the costs most visitors forget, like hotel taxes, airport taxis, the Skydeck, an architecture cruise and tipping, it's closer to $2,950. Use the calculator above to change any number to match your trip.
Winter is usually cheapest. KAYAK's data for hotels in the Loop shows January as the cheapest month and June as the most expensive. Summer festival and convention weeks push rates up, so check dates before you book. Source
It can be if you plan to see at least four of its stops. The pass costs $144 and covers Shedd Aquarium, Skydeck Chicago and three more choices, such as the Field Museum, the Art Institute or an architecture river tour. If you only want the Skydeck and one museum, single tickets cost less. Source
The CTA Blue Line runs from O'Hare to the Loop for $5, about $2.50 more than other stations. A taxi downtown is about $50 to $65 each way. From Midway, the Orange Line costs $2.50. Source
Chicago hotel taxes were already about 17.5%. Since May 1, 2026, most hotels with more than 100 rooms in the downtown tourism district add a 1.5% assessment too, bringing the total to about 19%. Source