Lakeside Holidays from NZ$3,873

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The Latest Lakeside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$4,297, price is now NZ$3,873 per person
NZ$3,873
per person
3 Aug - 6 Aug
found 11 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on 30 June 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,663, price is now NZ$5,321 per person
NZ$5,321
per person
3 Aug - 6 Aug
found 11 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The hotel is very clean Good air conditioning The staff is great The bar at the restaurant is very good The location is the best in Chicago Fancy neighborhood

Reviewed on 30 June 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,435, price is now NZ$3,900 per person
NZ$3,900
per person
3 Aug - 6 Aug
found 11 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good.

Reviewed on 30 June 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,523, price is now NZ$3,985 per person
NZ$3,985
per person
3 Aug - 6 Aug
found 11 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Nice clean room with minimalist/industrial vibe. Room was spacious. The front desk was helpful. The coffee shop was much appreciated.

Reviewed on 30 June 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was NZ$5,044, price is now NZ$4,520 per person
NZ$4,520
per person
3 Aug - 6 Aug
found 11 hours ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Staff was super friendly. The room was perfect and the view was exceptional. Would definitely stay here again.

Reviewed on 27 June 2026

Lakeside Holiday

Our pick of the best Lakeside Hotel Deals

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI
10/10 Exceptional! (144 reviews)
"Absolute paradise! The grounds are gorgeous with all of the plants and options for seating. Inside was cozy with everything we needed. We had dinner every evening in the screened in porch overlooking more gardens. Delightful!"

Reviewed on 17 June 2026

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Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Lakeside MI
9/10 Wonderful! (50 reviews)
"Really liked the layout, the added privacy of the studio was great though it could use a microwave, table or desk and a place to put clothes. The beach is great and the kayaks are a great added bonus."

Reviewed on 25 Sept 2025

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Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside MI
9.4/10 Exceptional! (68 reviews)
"Great place to stay - especially for a large family or friend group. Steps from the beach. Outstanding communication from property owner."

Reviewed on 16 June 2026

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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
See all 1,896 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.

Stay near popular Lakeside attractions

Burnison Galleries

Burnison Galleries showcases diverse works from regional artists in a welcoming Lakeside setting. Browse the curated collection at your leisure, with no admission fee required for this cultural Michigan experience.
See properties

Frequently asked questions

How much does a Lakeside holiday package cost?
Offering great value package deals from NZ$3,873 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.

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.