Winnetka Houseboats from CA $114

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Recommended hotels in Winnetka

A multi-story hotel with a modern design, featuring balconies with railings, large windows with curtains, and a parking area in front.

1. Heart O' Chicago

Edgewater

Hadell

CA $184 total

includes taxes & fees

Nov 8 - Nov 9

A modern hotel building with a large glass facade, a well-maintained lawn, and a clear blue sky.

2. Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

Nilantay Morshed

CA $220 total

includes taxes & fees

Nov 23 - Nov 24

A modern urban building with a distinctive curved facade, a prominent '10pin' sign, and a 'Tertius' restaurant on the ground floor.

3. Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

Safrona

CA $259 total

includes taxes & fees

Nov 22 - Nov 23

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

4. Claridge House Chicago, Tapestry Collection by Hilton

Downtown Chicago

Scott

CA $190 total

includes taxes & fees

Nov 22 - Nov 23

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

5. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Bonnie

CA $269 total

includes taxes & fees

Nov 23 - Nov 24

A building with a marquee reading 'ACME HOTEL COMPANY' and a sign stating 'ACME HOTEL NOT VACANCY'.

6. ACME Hotel Chicago, Outset Collection by Hilton

Downtown Chicago

alex

CA $142 total

includes taxes & fees

Dec 7 - Dec 8

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

7. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Jodi

CA $163 total

includes taxes & fees

Dec 7 - Dec 8

A multi-story building with a prominent entrance featuring a large archway and a sign.

8. Hilton Chicago

Downtown Chicago

Jordan

CA $223 total

includes taxes & fees

Nov 27 - Nov 28

A tall red brick building with a classic architectural style, surrounded by modern skyscrapers.

9. The Whitehall Hotel, BW Premier Collection

Downtown Chicago

Cinde

CA $136 total

includes taxes & fees

Dec 7 - Dec 8

A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

10. Swissotel - Chicago

Downtown Chicago

Oleg

CA $267 total

includes taxes & fees

Nov 26 - Nov 27

The exterior of a hotel named CAMBRIA, featuring a revolving door entrance, a signboard with the hotel name, and a visible parking rate sign.

11. Cambria Hotel Chicago Loop - Theatre District

Downtown Chicago

Tyrell

CA $179 total

includes taxes & fees

Nov 23 - Nov 24

A Hilton Garden Inn hotel with a modern facade, large windows, and a prominent sign.

12. Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Malessa

CA $140 total

includes taxes & fees

Nov 23 - Nov 24

A multi-story hotel with a prominent Courtyard Marriott sign, large windows, and a modern architectural design.

13. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Richard

CA $185 total

includes taxes & fees

Dec 6 - Dec 7

A modern hotel with a corner location, large windows, and a green awning.

14. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Tracy

CA $168 total

includes taxes & fees

Dec 8 - Dec 9

A modern hotel entrance with a neon sign, a covered walkway, and a cityscape view.

15. Moxy Chicago Downtown

Downtown Chicago

Lora

CA $204 total

includes taxes & fees

Nov 23 - Nov 24

A hotel facade with a grand entrance, large arched windows, and flags.

16. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Ebony

CA $200 total

includes taxes & fees

Dec 3 - Dec 4

A multi-story hotel with a modern facade, large windows, and a well-lit entrance.

17. The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

Downtown Chicago

Nolan

CA $259 total

includes taxes & fees

Nov 25 - Nov 26

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

18. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Melissa

CA $174 total

includes taxes & fees

Dec 7 - Dec 8

A modern high-rise building with a grid of windows and a mix of glass and concrete facades.

19. Hotel 505 River North

Downtown Chicago

Miya

CA $278 total

includes taxes & fees

Dec 8 - Dec 9

A modern high-rise building with a glass facade, surrounded by other tall buildings.

20. citizenM Chicago Downtown

Downtown Chicago

Kristopher Joel

CA $195 total

includes taxes & fees

Nov 23 - Nov 24

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Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theatre.

See all hotels in Winnetka

A suburban street with a stone house, a tree, and a clear sky.

Top reviews in Winnetka

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Bonnie

The entrance of L7 Hotels by Lotte, featuring a modern facade with large windows and a glass entrance.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Making people feel special must be their superpower because I was pleasantly surprised by a special gift I received for my birthday. The staff was always courteous, helpful and friendly. I loved that the lobby where they had a few games you could play but was so relaxing and quiet that there were several people just sitting around and chatting. It's proximity to the L had its pros and cons. The only con being the noise but it was so minimal that you only heard it while sitting on the window...

Lillian

Claridge House Chicago, Tapestry Collection by Hilton

Downtown Chicago

10/10 Excellent

Matthew

A cityscape with various buildings, including a prominent skyscraper and a historic structure with a dome.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Marc-André

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

10/10 Excellent

Steve

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

10/10 Excellent

Holly

A multi-story hotel with a prominent sign reading "FAREFIELD LNN & SUITES Marriott."

Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

10/10 Excellent

Kelly

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

This hotel is in a very convenient spot in Downtown Chicago. It's less than 4 minutes walking from Lasalle Station (blue line),Harrison Station (red line), and several bus lines. That means you can reach all the city's attractions quite easily. The staff was welcoming, professional, and always ready to help. The hotel itself is simple but beautiful and clean (the lobby and sitting area are both really nice). The room was cozy with a great view. Absolutely every corner of the room and the...

Alexandre

A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

Hyatt Place Chicago/River North

Downtown Chicago

10/10 Excellent

Andre

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

10/10 Excellent

Lauren

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

10/10 Excellent

Maegan A

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Things to do in Chicago
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Search Houseboats in Winnetka from CA $114

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Winnetka

1. Heart O' Chicago

2. Holiday Inn Chicago O'Hare – Rosemont by IHG

3. Hotel Chicago Downtown, Autograph Collection by Marriott

4. Claridge House Chicago, Tapestry Collection by Hilton

5. Sable at Navy Pier Chicago, Curio Collection by Hilton

6. ACME Hotel Chicago, Outset Collection by Hilton

7. DoubleTree by Hilton Chicago - Magnificent Mile

8. Hilton Chicago

9. The Whitehall Hotel, BW Premier Collection

10. Swissotel - Chicago

11. Cambria Hotel Chicago Loop - Theatre District

12. Hilton Garden Inn Chicago Downtown/Magnificent Mile

13. Courtyard by Marriott Chicago Magnificent Mile

14. Hampton Inn & Suites Chicago Downtown

15. Moxy Chicago Downtown

16. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

17. The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

18. Hilton Chicago/Magnificent Mile Suites

19. Hotel 505 River North

20. citizenM Chicago Downtown

Learn more about Winnetka

Top reviews in Winnetka

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

Explore a world of travel with Expedia