Lakeside Holidays from AU$2,184
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Your Lakeside Holiday
Our Lakeside holiday packages allow you to create your own adventure. Tailor your getaway to your interests and style and make every moment count in this wonderful city. A trip to Lakeside is an excellent opportunity to do some sightseeing. Make sure you visit popular attractions like Four Winds Casino New Buffalo, Warren Dunes State Park and New Buffalo Public Beach. Browse Expedia's extensive range of travel options and start planning your ultimate holiday to Lakeside now.
The Latest Lakeside Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was AU$3,172, price is now AU$2,184 per person
AU$2,184
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Wonderful staff! Convenient location for walking to restaurants, shopping and right next to a subway station
Reviewed on 30 Aug. 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug. 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug. 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,537, price is now AU$3,571 per person
AU$3,571
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The hotel was amazing. The staff were friendly. There is so much to do in the area.
Reviewed on 30 Aug. 2025
Level Chicago – Old Town
Downtown Chicago
Price was AU$3,524, price is now AU$2,340 per person
AU$2,340
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug. 2025
Lakeside Holiday
Lakeside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | South Bend Intl. Airport (SBN) |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Warren Dunes State Park, New Buffalo Public Beach and Warren Dunes State Park Beach |
Our pick of the best Lakeside Hotel Deals
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 2 Sept to 3 Sept
AU$199
2 Sept - 3 Sept
includes taxes & fees
Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.