South Wayne Holidays

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South Wayne Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was S$3,839, price is now S$2,719 per person
S$2,719
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,369, price is now S$2,983 per person
S$2,983
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on 18 Aug, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,258, price is now S$2,932 per person
S$2,932
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Great view of the lake and city

Reviewed on 18 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$5,300, price is now S$3,680 per person
S$3,680
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$3,827, price is now S$2,741 per person
S$2,741
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug, 2025

Top hotels in South Wayne

Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is S$139 per night from 7 Sept to 8 Sept
S$139
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (676 reviews)
"Property was clean and close to highway."

Reviewed on 1 Aug, 2025

Baymont by Wyndham Freeport
Darlington Inn

Darlington Inn

2 out of 5
201 Christiensen Dr, Darlington, WI
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 24 Aug to 25 Aug
S$111
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (408 reviews)
Great service and room!
"Our first room was a bit damp so they moved us to a very nice suite room. It was comfortable and well appointed. They went to great lenghts to make sure we were comfortable. We would definitely stay there again."

Reviewed on 14 Aug, 2025

Darlington Inn
AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is S$159 per night from 7 Sept to 8 Sept
S$159
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (361 reviews)
"Only complaint is that the room was poorly lit...only 2 table lamps for the main area. Otherwise an excellent stay."

Reviewed on 9 Aug, 2025

AmericInn by Wyndham Monroe
See all 131 properties in South Wayne
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.

Frequently asked questions

How much does a South Wayne holiday package cost?
You can snap up a holiday package to this popular destination from S$2,719 on Expedia. However, how much your holiday to South Wayne costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to South Wayne?
If you're hoping to score a cheap South Wayne holiday package, consider planning a trip in January, February and November. You'll usually find lower rates on accommodation and flights during these months — perfect for budget-conscious travellers.
How many days is enough for South Wayne?
The ideal length of your South Wayne holiday depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to visit all the main sights and explore some hidden spots along the way.
How to find the best South Wayne package deals?
Start your search for a South Wayne package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal South Wayne package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your South Wayne adventure underway.
Is it cheaper to book a South Wayne holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and stays separately. Better still, you can tailor your South Wayne escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to South Wayne?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment South Wayne escape.
How to plan a trip to South Wayne?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit South Wayne.
  2. Budget wisely: On top of the price of your stay, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to South Wayne.
  3. Decide how long to go for: Now that you're up to speed on South Wayne, you can figure out the perfect length of your break. Put together a rough plan and give yourself enough time to cover everything you want to see.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, book the perfect South Wayne holiday package for you.

* 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.