
Lakeside 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
Lakeside Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.


Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
It’s not what I was expecting, I was expecting something different , no views, not happy at all
Reviewed on 14 Jul, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Great location, but the $50.00 early check-in fee is ridiculous. Also, the comforter on the bed has seen better days.
Reviewed on 15 Jul, 2025

Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.
Reviewed on 15 Jul, 2025
Top hotels in Lakeside

Blue Chip Casino Hotel and Spa
777 Blue Chip Drive, Michigan City, IN
8/10 Very Good! (1,595 reviews)
Visited Michigan City for my birthday
"I was pleasantly surprised by the staff in all areas. The housekeeping staff, restaurants staff and hotel staff were all very friendly and ready to assist if needed."
Reviewed on 12 Jul, 2025

Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,388 reviews)
"Great place and staff!"
Reviewed on 13 Jul, 2025

Baymont by Wyndham New Buffalo
18800 Harbor Country Drive, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is S$115 per night from 11 Aug to 12 Aug
S$115
11 Aug - 12 Aug
includes taxes & fees
6.6/10 (1,021 reviews)
"Is a good place to stay"
Reviewed on 14 Jul, 2025
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
* 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.