Flexible plans
Chicago trips built around a convention or a game can move. Book a rate you can drop, and note when the free window closes.
from $69/night984 hotels compared
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984 hotels compared
Chicago sits on Lake Michigan, and the Loop holds most of its famous architecture and museums. Pick the Loop for the big sights, River North for restaurants, or a neighborhood near an L stop for bars and shops away from the office towers.
Millennium Park, the Art Institute of Chicago and the theater district are all in the Loop. The Chicago River runs along its north edge, with the Riverwalk below the bridges. Many CTA lines meet downtown, so a Loop hotel still works when half your plans are in other neighborhoods.
Across the river, River North has galleries, restaurants and plenty of hotels. Streeterville and the Magnificent Mile run east toward Navy Pier and the lake. The West Loop and Fulton Market have the restaurants near Union Station and the Blue, Green and Pink lines. The lake is farther away from there.
Lincoln Park has the zoo, leafy streets and North Avenue Beach. Lakeview, farther north, has Wrigley Field and the Belmont and Addison L stops. Wicker Park and Logan Square are on the Blue Line toward O’Hare, with shops and music venues well away from the downtown hotel blocks.
Hyde Park, with the University of Chicago and the Griffin Museum of Science and Industry, is a separate trip south from downtown. Summer is the season for the lakefront and outdoor events. Winter is cold, windy and often snowy. Look up the CTA station nearest your hotel before you plan airport or neighborhood trips.
Millennium Park, the Art Institute and the theaters are mixed in with the Loop’s office towers. Most CTA lines meet here, and Union Station is on the west side of downtown. Some blocks go quiet after office hours, so look at the street before you book if you want a late night out.
Around here: Millennium Park, Art Institute of Chicago, Chicago Theatre
River North has the restaurants and galleries just north of the Chicago River. To the east, the Magnificent Mile and Streeterville lead to Navy Pier. Stay here for dinners and lakefront walks. The Art Institute is across the river in the Loop, and Museum Campus is past it.
Around here: Chicago Riverwalk, Magnificent Mile, Navy Pier
Fulton Market and Randolph Street fill up with diners in the evening. Union Station and Ogilvie are close. The lakefront is not. Green and Pink line stops cover part of the area. The West Loop is bigger than its restaurant strip, so a hotel at the far end can be a long walk from the train.
Around here: Fulton Market, Randolph Street, Union Station
On the north side, Lincoln Park has the zoo and North Avenue Beach. Farther north, Lakeview has Wrigley Field and the bars along Clark Street. Stay near a Red or Brown Line stop for trips downtown. Museum days start with a train ride.
Around here: Lincoln Park Zoo, North Avenue Beach, Wrigley Field
Wicker Park’s shops, restaurants and music venues line Milwaukee Avenue near the Damen Blue Line stop. Logan Square is farther northwest on the same line. Both are a straight ride to O’Hare. The lakefront takes a transfer or a longer trip.
Around here: Damen Blue Line station, The 606, Logan Square
The University of Chicago, the Griffin Museum of Science and Industry and Jackson Park are on the South Side, well south of the Loop hotels. Stay in Hyde Park if you’re here for the university or the museum. Metra Electric and buses run downtown.
Around here: University of Chicago, Griffin Museum of Science and Industry, Jackson Park
Riverwalk, beach and park days are easiest from late spring to early fall. At O’Hare, the average high is near 85°F in July and near 32°F in January. The lakefront often feels cooler. In winter, pack a warm coat and leave slack in the schedule for snow.
O’Hare International Airport is northwest of downtown and Midway is southwest. CTA trains reach the Loop from both airports. Amtrak arrives at Union Station, west of the river.
17 mi from downtown
The CTA Blue Line runs directly from O’Hare to the Loop around the clock. The airport station connects to Terminals 1, 2 and 3; Terminal 5 passengers use the airport shuttle train.
10 mi from downtown
The CTA Orange Line runs from the airport station to the Loop. It does not run overnight. If you land late, sort out another way downtown before you book.
When a Wrigley Field game, a convention or a winter flight could change your dates.
No. Free cancellation runs out on a date set by your rate. Read that date before you pay.
The Loop. Several CTA lines meet there, and Millennium Park and the theaters are close. River North is better if dinners and the river are the main plan.
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