Winnetka Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Winnetka Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Downtown Chicago
Price was S$2,686, price is now S$2,396 per person
S$2,396
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,201 reviews)
We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.

Reviewed on 9 Mar, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on 10 Mar, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (2,002 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.

Reviewed on 9 Mar, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$2,908, price is now S$2,595 per person
S$2,595
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Room was clean, I was super close to everything. The staff was very friendly! Can’t wait to come back

Reviewed on 11 Mar, 2026

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top hotels in Winnetka

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$249 per night from 21 Mar to 22 Mar
S$249
21 Mar - 22 Mar
includes taxes & fees
8/10 Very Good! (9,942 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.

Reviewed on 10 Mar, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is S$242 per night from 24 Mar to 25 Mar
S$242
24 Mar - 25 Mar
includes taxes & fees
9.4/10 Exceptional! (3,510 reviews)
Clean, amazing terrace, bad and breakfast.

Reviewed on 10 Mar, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is S$183 per night from 22 Mar to 23 Mar
S$183
22 Mar - 23 Mar
includes taxes & fees
8.6/10 Excellent! (5,725 reviews)
Great location. Room was very hot. U can't switch heat to AC in the rooms. U just have to deal with what the hotel has it on. Also they would only give us one little fan to cool off. Not 2 which I'm sure they had plenty of. Other then that no complaints. They give a free happy hour with 2 free drinks ...

Reviewed on 11 Mar, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,662 properties in Winnetka
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Winnetka

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$33
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$56
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Winnetka

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.