Lakeside Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
No refrgerator, can hear the noise coming from the street. Room us clean and smell good

Reviewed on 14 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
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

Virgin Hotels Chicago

4.5 out of 5
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 3 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
I didn't like property didn't have free parking.

Reviewed on 15 Jul, 2025

Top hotels in Lakeside

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
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

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Blue Chip Casino Hotel and Spa
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
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

Get rates
Four Winds Casino Resort – New Buffalo
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

2.5 out of 5
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

Baymont by Wyndham New Buffalo
See all 1,856 properties in Lakeside
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 Lakeside holiday package cost?
Offering great value package deals from S$437 on Expedia, you'll be pleasantly surprised at how much a holiday to Lakeside costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Lakeside?
To pick up cheap Lakeside holiday packages, plan your trip outside of peak periods like public holidays and major festivals. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Lakeside?
Typically, a handful of days is enough to check out the major attractions during your Lakeside holiday. But if you'd like to have some time to kick back or go on day tours, think about extending your itinerary.
How to find the best Lakeside package deals?
Use Expedia's filters to find some great Lakeside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Lakeside package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Lakeside holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Lakeside holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Lakeside?
Score amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Lakeside break.
How to plan a trip to Lakeside?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Lakeside.
  2. Set your budget: Factor in costs such as flights, food and transportation when calculating how much to set aside for your trip to Lakeside. Then, pick a hotel that fits your budget, whether that's a wallet-friendly stay or a high-end getaway.
  3. Decide your trip length: Think about how long you'd like to spend exploring Lakeside. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Lakeside holiday package that brings all your bookings together.

* 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.