Historic Hotels in Chicago

The neighborhoods

Where to stay, by area

The Loop

Chicago’s central business district, named for the cable-car line that once circled it; the elevated L tracks still form a loop around downtown. Millennium Park, the Chicago Riverwalk, the Theatre District and State Street shopping are all here, and it makes a walkable base.

Historic hotels here: the Palmer House, Staypineapple in the Reliance Building and the Silversmith on Jewelers Row; Kimpton Gray on LaSalle Street; the Allegro in the Theatre District; the Union League Club on Jackson Boulevard; and Pendry Chicago on Michigan Avenue by the river.

South Michigan Avenue

A one-sided street of hotels, clubs and cultural buildings from 1882 to 1930, facing Grant Park and Lake Michigan between 11th and Randolph Streets. The city made it a landmark district, the Historic Michigan Boulevard District, in 2002. Grant Park and the Museum Campus are across the street.

Four historic hotels line it: the Chicago Athletic Association across from Millennium Park, then the Congress Plaza, the Blackstone and Hilton Chicago.

Magnificent Mile and Streeterville

The Magnificent Mile, North Michigan Avenue’s shopping street, runs from the river bridge past the Water Tower, one of the few buildings to survive the 1871 fire. Streeterville, to the east, has Navy Pier, the Museum of Contemporary Art and the lakefront.

LondonHouse stands at the bridge, the InterContinental and the Warwick Allerton are on the avenue, and The Drake is at its north end.

River North

A dense district of art galleries and studios in former warehouses, with one of the city’s busiest nightlife scenes. Its landmarks include Marina City and Mies van der Rohe’s 330 N. Wabash, the former IBM Building, where The Langham occupies the lower floors.

Gold Coast

One of the country’s most affluent neighborhoods, near the lakeshore, with streets of historic mansions, designer boutiques and restaurants, and a late-night bar scene on Rush Street. The Gold Coast Historic District, listed on the National Register in 1978, runs roughly from North Avenue to Oak Street between Clark Street and Lake Shore Drive.

The Ambassador Gold Coast sits inside the district. The Drake, on Walton Place, is where the Gold Coast meets the north end of the Magnificent Mile.

Old Town, Lincoln Park and Wicker Park

Neighborhood bases outside downtown, each with a National Register district: the Old Town Triangle (1984) by Lincoln Park, and Wicker Park (1979), with its Victorian streets. The Robey fills Wicker Park’s 1929 Art Deco Northwest Tower, where Damen, Milwaukee and North Avenues meet. No hotel in Old Town or Lincoln Park has passed our checks yet.

Before you book

Planning your stay

Getting around

Downtown is walkable, and the CTA’s L trains cover the rest. A ride is $2.50 by Ventra card or contactless payment, transfers within two hours are free, and passes cost $5 for one day, $15 for three and $20 for seven. The Blue Line runs 24 hours from O’Hare to downtown in about 45 minutes ($5 from O’Hare), and the Orange Line reaches Midway in about 25 minutes ($2.50). A taxi from O’Hare is about $40.

Parking

Few downtown historic hotels have free parking; expect valet or a nearby garage, charged by the night. The Blackstone, for example, charges $82 a night for valet and $72 to park yourself. Many visitors skip the car and take the L.

When to go

Summer, June to August, is peak season, with the warmest weather, lakefront beaches, festivals such as Lollapalooza and the highest hotel prices. Spring and fall are milder shoulder seasons, and fall brings the Chicago Marathon in October and post-summer hotel deals. January and February are the cheapest months, with average highs around 30 to 38°F.

Accessibility

All CTA buses and trains are accessible, and 110 of the 146 rail stations are; check the CTA’s elevator alerts before you ride. Historic buildings vary, so ask each hotel about accessible rooms and elevator access when you book.

Before you book

Budget for taxes: the combined hotel tax is about 17.4% (the city’s 4.5% plus state, Cook County, MPEA and sports-authority taxes), and since May 1, 2026, hotels with 100 or more rooms in downtown ZIP codes add a 1.5% Tourism Improvement District charge. Check nightly add-ons too: the Chicago Athletic Association charges a $31.96 destination fee, while The Drake and the Congress Plaza advertise none. The Robey adds a nightly facilities fee and requires guests to be 21 to check in.