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A serene lake with reflections of trees and a cloudy sky.

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    Check prices for these dates

    Check prices for these dates, December 14 – 15, 2026

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    Our top choices for Crestwood condo rentals

    1. Chic Suite/Mins to L Train /Laundry/Free Parking

    A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

    2. Fully-Equipped Suite | Gym Access

    A stone building with a covered entrance, benches, and potted plants.

    3. King Bed Suite | Indoor Pool. Free Breakfast.

    A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

    4. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

    Private kitchen

    5. Air-Conditioned King Suite | Complimentary Breakfast

    A stone building with a covered entrance, benches, and potted plants.

    6. Fully-Equipped Suite | Complimentary Breakfast

    A stone building with a covered entrance, benches, and potted plants.

    7. Free Breakfast. Indoor Pool. Gym. Business Center.

    A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

    8. 2 Bedroom | Free Daily Breakfast. Indoor Pool.

    A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Crestwood

    Explore the sprawling Playfield Park where locals gather for weekend softball tournaments and picnics under shady oak trees. Visit Caesar Park's splash pad in summer, then grab a slice at the family-owned Aurelio's Pizza that's been serving locals since 1959.

    See all hotels in Crestwood

    A serene lake with reflections of trees and a cloudy sky.

    Top reviews in Crestwood

    Holiday Inn Express Crestwood by IHG

    A modern lobby with a reception desk, a sofa, and large windows offering a view of the outside.

    Hilton Vacation Club Hotel Blake Chicago

    A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

    Sable at Navy Pier Chicago, Curio Collection by Hilton

    An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

    Hyatt Regency Chicago

    A spacious bar area with high ceilings and large windows, offering views of a cityscape.

    L7 CHICAGO by LOTTE HOTELS

    A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

    SureStay Plus Hotel by Best Western Chicago Lombard

    A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

    ACME Hotel Chicago, Outset Collection by Hilton

    A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

    Hampton Inn Majestic Chicago Theatre District

    A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

    citizenM Chicago Downtown

    A modern building with a colorful facade and a red circular seating area.

    Fairfield Inn & Suites Chicago Downtown/River North

    A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

    Hilton Chicago/Magnificent Mile Suites

    A cityscape at dusk with high-rise buildings, including a Hilton hotel.

    Claridge House Chicago, Tapestry Collection by Hilton

    The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

    Canopy by Hilton Chicago Central Loop

    A spacious lobby with a long bar area, red curtains, and a patterned carpet.

    Hyatt House Chicago/West Loop-Fulton Market

    A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

    DoubleTree by Hilton Chicago - Magnificent Mile

    A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

    Hampton Inn & Suites Chicago Downtown

    A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

    Hyatt Place Chicago/River North

    A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

    LIVN - West Loop Chicago

    A cozy room with a sofa, a dining table, and a window with a view of buildings.

    Hampton Inn Chicago West Loop Fulton Market Area

    An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

    Swissotel - Chicago

    A dining table set for six with a cityscape view through large windows.

    Frequently Asked Questions

    Why book your condo in Crestwood with Expedia?

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    How can I find cheap condos in Crestwood?

    The best way to find cheap condos in Crestwood is with Expedia's easy-to-use filter tool. Refine your search results by star rating, amenities and budget to land awesome rates in a couple of clicks.

    What is there to do in Crestwood near my condo?

    The most practical travel accessory is a well-planned to-do list. Hollywood Park is a wonderful spot to start your adventures in Crestwood.

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