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Vacation rentals (16)

16 properties found

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  • Hollywood Rentals Llc

    Hollywood Rentals Llc

    Homestay

    Average

    (373 reviews)

    5.6
    Located 15 km from Chicago Union railway station, Hollywood Rentals Llc Chicago apartment is merely a 9-minute walk from the Swedish American Museum.

    starts from

    US$ 70 per one night

  • 5430 Happy Home

    5430 Happy Home

    Homestay

    Good

    (430 reviews)

    8
    5430 Happy Home Chicago apartment is located 10 minutes by car from the Guaranteed Rate Field and 3.7 km from the Lakefront Trail. This homestay is situated 11 km from Chicago Union train station and…

    starts from

    US$ 29 per one night

  • Hyde Park Modern Private Room - Near Univ Of Chicago

    Hyde Park Modern Private Room - Near Univ Of Chicago

    Homestay

    Good

    (2 reviews)

    8
    Hyde Park Modern Private Room - Near Univ Of Chicago is situated a 6-minute walk from Gallery Guichard and 15 km from Chicago Midway International airport. This homestay is situated 11 km from…

    starts from

    US$ 102 per one night

  • A Hidden Gem, Approx 15 Mins To Downtown Chicago!

    A Hidden Gem, Approx 15 Mins To Downtown Chicago!

    Homestay

    Excellent

    (24 reviews)

    9
    Situated around a 10-minute ride from the Ridgeland Common Ice Arena, the 1-room A Hidden Gem, Approx 15 Mins To Downtown Chicago! Apartment also boasts easy access to Chicago Union train station…

    starts from

    US$ 88 per one night

  • Afrique Francaise De Woodlawn 1

    Afrique Francaise De Woodlawn 1

    Homestay

    Excellent

    (19 reviews)

    9
    To enjoy your vacation in Chicago, stay at the 1-room Afrique Francaise De Woodlawn 1 Apartment Chicago, which is about a 10-minute ride from the Promontory Point Park and about 700 metres from White…

    starts from

    US$ 32 per one night

  • Close To Downtown - Free Parking

    Close To Downtown - Free Parking

    Homestay

    Good

    (7 reviews)

    7.4

    starts from

    US$ 34 per one night

  • Fully Furnished Bedroom Near Medical District And Uic

    Fully Furnished Bedroom Near Medical District And Uic

    Homestay

    Excellent

    (10 reviews)

    8.6
    Situated around a 25-minute walk from the United Center, the 2-room Fully Furnished Bedroom Near Medical District And Uic Chicago apartment provides guests with Wi-Fi for either business or leisure.

    starts from

    US$ 50 per one night

  • The Lyons' Den

    The Lyons' Den

    Homestay

    Excellent

    (12 reviews)

    9.8
    To enjoy your vacation in Chicago, stay at the 15 m² The Lyons' Den Apartment Chicago, which is around 6 km from the 35-acre beautifully landscaped Lincoln Park Zoo and approximately a 25-minute walk…

    starts from

    US$ 219 per one night

  • Beautiful Home Near Downtwon - Free Parking!

    Beautiful Home Near Downtwon - Free Parking!

    Homestay

    Excellent

    (8 reviews)

    8.6
    The 7-room Beautiful Home Near Downtwon - Free Parking! Chicago apartment is located within a 9-km distance of Chicago Union train station and in close proximity to House of Prayer for All People.

    starts from

    US$ 48 per one night

  • A Secluded Bedroom With A Private Full Bathroom

    A Secluded Bedroom With A Private Full Bathroom

    Homestay

    Excellent

    (20 reviews)

    9
    To enjoy your vacation in Chicago, stay at the 1-room A Secluded Bedroom With A Private Full Bathroom Chicago apartment, which is 850 metres from the private research University of Chicago and nearly…

    starts from

    US$ 135 per one night

  • Amazing Place To Stay Near Downtown Chicago!

    Amazing Place To Stay Near Downtown Chicago!

    Homestay

    Excellent

    (6 reviews)

    8.8
    Amazing Place To Stay Near Downtown Chicago! apartment is situated a 6-minute walk from Pillar Of Truth Evanglistic Church Of God In Christ and 5 km from Chicago Midway International airport. Wi-Fi…

    starts from

    US$ 45 per one night

  • Cosy Room Near Medical District With Private Balcony

    Cosy Room Near Medical District With Private Balcony

    Homestay

    Excellent

    (12 reviews)

    8.2
    Cosy Room Near Medical District With Private Balcony Chicago is located 6 km from the super-tall skyscraper "Willis Tower" and 16 minutes' walk from the Douglas Park. The homestay is situated within…

    starts from

    US$ 49 per one night

  • Wonderful Home Close To Downtown Chicago - Free Parking

    Wonderful Home Close To Downtown Chicago - Free Parking

    Homestay

    Good

    (12 reviews)

    7

    starts from

    US$ 44 per one night

  • Kenwood Apartments, Downtown Hyde Park

    Kenwood Apartments, Downtown Hyde Park

    Homestay

    Good

    (73 reviews)

    6.8
    To enjoy your vacation in Chicago, stay at Kenwood Apartments, Downtown Hyde Park Chicago, which is approximately 2 km from Treasure Island Foods and just 12 minutes' walk from the Rockefeller…

    starts from

    US$ 87 per one night

  • Afrique Francaise De Woodlawn 2

    Afrique Francaise De Woodlawn 2

    Homestay

    Good

    (16 reviews)

    7.4
    The 100 m² Afrique Francaise De Woodlawn 2 Apartment Chicago is situated 6 minutes' walk from first house of prayer and 15 km from Chicago Midway International airport. The homestay is situated 14 km…

    starts from

    US$ 97 per one night

  • Drexel Apartments, Downtown Hyde Park

    Drexel Apartments, Downtown Hyde Park

    Homestay
    To enjoy your vacation in Chicago, stay at Drexel Apartments, Downtown Hyde Park Chicago, which is within 4 km of the Burnham Park and within 10 minutes' drive of the Sprawling hands-on Museum of…

    starts from

    US$ 50 per one night

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Hotels in Chicago

Chicago's vibrant cityscape boasts 1,262 hotels, offering a range of accommodations to suit any traveler. Downtown's Loop and Near North Side are home to many hotels, with notable 3-star accommodations averaging $150 per night and luxurious 5-star options around $450. New additions, like the fresh yet luxurious 'The Hoxton,' add charm with their innovative design. Discover your ideal stay and book effortlessly through our platform.

Where to stay in Chicago - a guide to the best areas and neighborhoods

Hotel Name
Description

Hotel Lincoln

* Lincoln Park Zoo offers free admission and is great for kids.

* The area has expansive parks perfect for picnics and family outings.

* Nearby family-friendly restaurants and activities make it convenient for all ages.

Families should consider Lincoln Park for its family-friendly attractions and green spaces.

Palmer House

* Key business centers and corporate offices are just a walk away.

* Public transportation hubs are conveniently located for easy commuting.

* Hotels like the Palmer House offer conference facilities and business services.

Business travelers find The Loop ideal due to its centrality and business amenities.

Freehand Chicago

* Galleries and museums make it great for art lovers traveling alone.

* River North hosts a vibrant nightlife scene perfect for meeting new people.

* The Freehand Chicago offers shared and private rooms, ideal for solo stays.

Solo travelers can enjoy exploring River North, known for its culture and community vibe.

The Drake Hotel

* Beautiful historic architecture and scenic walks make it a romantic spot.

* High-end shopping and fine dining add a luxurious touch to your stay.

* The Drake Hotel offers elegance and romantic settings for couples.

Couples on a romantic getaway should explore the Gold Coast for its upscale charm.

Holiday Jones Hostel

* The district offers budget-friendly dining and entertainment venues.

* Hostels and lower-cost hotels provide economical accommodation choices.

* Local markets and boutiques offer unique yet affordable shopping experiences.

Budget travelers might find great value in Wicker Park, known for its affordable options.

Chicago Tips You Must Know

* Best times to book: Aim to book at least a month in advance for the best deals, especially for weekends and major holidays like Thanksgiving when prices can soar.

* Seasonal considerations: Peak tourist seasons include summer months and times around major events like Lollapalooza and the Chicago Marathon, leading to higher prices and limited availability.

* Transportation advice: Utilize Chicago's efficient CTA system, with single rides costing around $2.50 and unlimited day passes available for $10 for easy city navigation.

* Money-saving tips: Opt for the CityPASS to see multiple attractions at a discount, and dine at local markets for affordable, delicious meals.

* Additional practical advice: Stay cautious in less busy areas at night, particularly in certain parts of the South Side and West Side.

Frequently asked question

Which hotels in Chicago offer the best views of Lake Michigan?

The Swissotel Chicago offers stunning panoramic views of Lake Michigan from its rooms.

Are there any Chicago hotels with easy access to the city's beaches?

The W Chicago - Lakeshore is just steps away from Oak Street Beach, making it perfect for beach lovers.

What hotels in Chicago are near major attractions like Millennium Park and Navy Pier?

The Radisson Blu Aqua Hotel offers proximity to Millennium Park and Navy Pier within walking distance.

Which Chicago hotels provide adventure and activity options nearby?

The Kimpton Hotel Palomar Chicago is close to River North, where guests can explore art galleries and experience vibrant nightlife.

What is the best time of year to book hotels in Chicago for good weather and events?

Summer, particularly from June to September, is ideal for booking hotels to enjoy Chicago's festivals and pleasant weather.

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