Lakeside Holidays

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    Better together

    Save up to €185 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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    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Lakeside

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Great hotel, very clean. They could add a bar in the lobby and one more elevator

Reviewed on 4 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Very friendly staff, hotel needs renovation. Pool dated some stones missing by pool & ceiling needs painting.

Reviewed on 4 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
London house did not disappoint. View room was a highlight, staff were friendly and courteous. Close walk to Riverwalk, tours, parks, museums and shops. Make reservations for LH rooftop. I only wish I was able to get credit with Hilton for the stay.

Reviewed on 3 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on 1 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Top hotels in Lakeside

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
9.2/10 Wonderful! (52 reviews)
"Great rental for multiple families. It was terrific having a pool and the beach was wonderful and close by."

Reviewed on 30 Jul 2025

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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
The price is €143 per night from 17 Aug to 18 Aug
€143
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (1,639 reviews)
"My bestie and I have been staying at the Blue Chip for 10 plus years. The staff is so friendly, accommodating and all around excellent."

Reviewed on 2 Aug 2025

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! (1,434 reviews)
"Everybody was very friendly and helpful. Our room was the cleanest hotel room I've ever stayed in and was lovely!"

Reviewed on 2 Aug 2025

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Four Winds Casino Resort – New Buffalo
See all 1,865 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 €777 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.