
Lakeside Vacation Packages
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Your Lakeside Vacation
With a Lakeside vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your journey has been taken care of before you depart, so you can make the most of your time discovering this exciting city. Fill your schedule with tours of Four Winds Casino New Buffalo, New Buffalo Public Beach and Warren Dunes State Park Beach, some of the attractions you shouldn't miss during a trip to Lakeside. Browse Expedia's wide range of travel options and start planning your dream vacation to Lakeside today.
Top Lakeside Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,101, price is now CA $778 per person
CA $778
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on Jul 11, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,912, price is now CA $1,393 per person
CA $1,393
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Perfect location Perfect view excellent staff fun time had by wife for her birthday great little getaway thanks
Reviewed on Jul 11, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $3,029, price is now CA $2,213 per person
CA $2,213
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026

The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,375, price is now CA $1,034 per person
CA $1,034
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
Very nice rooms and excellent service. Our stay could not have been better!
Reviewed on Jul 11, 2026
Lakeside Hotel Deals

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 Jun 17, 2026

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Lakeside MI
9/10 Wonderful! (51 reviews)
"We truly enjoyed our stay over the holiday weekend. We were a group of a adults so it was lovely that rooms gave us our own personal space but the large common area was wonderful when we all wanted to be together. Private beach access was great and the short walk was even better. We’d happily stay ..."
Reviewed on Jul 10, 2026

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 Jun 16, 2026
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
Frequently asked questions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







