Magnificent Mile
Four Seasons Hotel Chicago
Largest standard rooms and the city's best service
Explore Hotel
A little local perspective
Worth knowing.
Worth going.
- Destination
- Chicago, Illinois, USA
- The selection
- 12 hotels
- Your kind of trip
- architecture · food · museums · city break
$$$ — roughly $300-800 a night, peaking May to October
Chicago has two waterfronts and they do completely different things.
The lake is the big one: Lake Michigan stretches to the horizon like a sea, with 29 miles of public shoreline, a continuous lakefront path, beaches in the middle of the city and no private development between the buildings and the water. That was a deliberate decision made in the nineteenth century and it is the single best thing about the city.
The river is the small one, and it is where the architecture is. The Chicago River runs through the Loop in a Y, lined by the towers that made the city the birthplace of the skyscraper, with a Riverwalk along its south bank and boat tours running all summer.
Which frontage, and the walk between them
They are about a kilometre apart at the closest point, which means the answer for most visitors is somewhere between them.
That zone is the Magnificent Mile and the near North Side: north of the river, east of Michigan Avenue, with the lake at the end of the street and the Loop across the bridge. From there the Art Institute is a fifteen-minute walk south, Millennium Park is on the way, the architecture boat leaves from the river below you, and Oak Street Beach is five minutes east.
Staying further out, in the West Loop or Wicker Park, gets you the best restaurants in the city and puts a train between you and the water.
The twelve below are grouped by which side of the river they sit on.
North of the river, the Magnificent Mile
Between the river and the lake. The default answer, and the most walkable part of Chicago.
Four Seasons Hotel Chicago occupies a tower with the largest standard rooms in the city, an enormous spa and a level of service that has been the American benchmark for two decades. It is the best hotel in Chicago.
The Langham, Chicago sits on the river in a Mies van der Rohe building, with a spa, floor-to-ceiling glass over the water and an interior of considerable quality. It is the most architecturally serious hotel here.
The Peninsula Chicago occupies the upper floors of a Michigan Avenue tower with lake views, a very good bar and rooms that are among the largest on the Mile.
Waldorf Astoria Chicago sits in a French-inspired building on a quiet street off the Mile with a courtyard and the most residential feel of the group.
St. Regis Chicago occupies the top floors of a new supertall on the river with the highest hotel rooms in the city and a bar to match.
The Drake sits on Michigan Avenue in the 1920s landmark at the top of the Mile, facing the lake, and it is the city's grand hotel and the home of a very old cocktail lounge.
The Gwen, a Luxury Collection Hotel occupies a 1929 Art Deco building on the Mile with a rooftop bar and rooms with the best value views on this stretch.
Viceroy Chicago sits a block from the water with a rooftop pool over the lake, contemporary rooms and a design-led interior.
South of the river, the Loop
The business core, the theatre district and the museums along Grant Park.
Chicago Athletic Association Hotel occupies the 1893 Chicago Athletic Association building on Michigan Avenue facing Millennium Park, with a games room, a rooftop bar over the park and interiors that are the most enjoyable public spaces of any hotel in the city.
LondonHouse Chicago sits on the river at Michigan Avenue in a 1923 Beaux-Arts building with a rooftop that has the best river-and-lake view in Chicago.
Pendry Chicago occupies a converted building in the Loop with a rooftop pool and rates below the Mile hotels.
The West Loop
Nobu Hotel Chicago sits in the West Loop among the best restaurants in the country, with a rooftop and a design-led interior. It is fifteen minutes from the lake and at the centre of the city's food.
What we have left off
The hotels around O'Hare and the convention centre at McCormick Place are excluded. They exist to serve flights and trade shows, they are cheaper for that reason, and they are a long train ride from both the river and the lake.
What to do
Take the architecture boat tour on the river. It is the best introduction to any American city and it explains why Chicago looks the way it does.
Walk or cycle the lakefront path. Rent a bike and go north to Lincoln Park or south past the Museum Campus.
The Art Institute is one of the great museums in the world and deserves a full morning. Millennium Park and the Bean are next door.
Eat properly. Deep dish once, out of the way, and then the West Loop, which has as concentrated a run of serious restaurants as anywhere in America.
Go up something. The Willis Tower Skydeck and 360 Chicago both work; the 360 has the better view because it includes the Willis Tower.
Practical notes
O'Hare connects on the Blue Line to the Loop in about 45 minutes; Midway on the Orange Line in 25.
May, June, September and October are the best months. July and August are hot, humid and busy. Winter is genuinely cold, with wind off the lake, and the city is cheap and the museums are empty.
The L is straightforward and the Loop is walkable. A car is unnecessary and parking is expensive.
Explore 4 & 5 Star Chicago Hotels
Prices shown are sample rates from upcoming dates — not quotes for specific dates. Open a hotel and choose your own dates and guests to see the exact price.
Questions people actually ask
River or lake?
Stay between them on the near North Side and you have both. It is a kilometre from one to the other.
Is the West Loop worth it?
For a food-focused trip, yes. It is fifteen minutes from the waterfronts and the restaurants are the best in the city.
Is Chicago worth visiting in winter?
It is very cold and very cheap, and the architecture and museums are indoors. February in Chicago is an underrated proposition.
How many nights?
Four. Three for the city and a fourth for the neighbourhoods.
