Exclusive Lake Michigan Vacation Deals

Lake Michigan vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,126, price is now CA $812 per person
CA $812
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,177, price is now CA $861 per person
CA $861
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Price was CA $3,751, price is now CA $2,782 per person
CA $2,782
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Chicago (ORD)
Stay at this aparthotel in Chicago. Enjoy free WiFi and housekeeping. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,227, price is now CA $920 per person
CA $920
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,342, price is now CA $1,020 per person
CA $1,020
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,277, price is now CA $1,757 per person
CA $1,757
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Frequently asked questions

How much are vacation packages to Lake Michigan?
Adventure awaits in Lake Michigan, with Travelocity vacation packages from as low as CA $812. Including hotels and flights, these great deals make it really easy to experience all corners of the world.
Where can I get the best vacation package deals for Lake Michigan?
There are excellent Lake Michigan package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 665,000 worldwide properties? Remember this when you're ready to check another place off your must-see list.
Why should I purchase my Lake Michigan vacation package with Travelocity?
From our 24/7 support to our range of fantastic destinations, we're committed to giving you the vacation of a lifetime. All you need to do is to click and book — our Price Match Guarantee will make sure you lock in the lowest price.
Can I go on vacation to Lake Michigan at this time?
Don't plan your trip to Lake Michigan without the facts about quarantine policies and travel restrictions. Travelocity's Covid-19 Travel Advisor will fill in the blanks. Our travel experts have pulled together all the info you need to make your vacation as hassle-free as possible.

Top Lake Michigan hotel deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $249 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue Sheboygan WI
Free cancellation
Reserve now, pay when you stay
The price is CA $173 per night
CA $173
CA $196 total
Dec 16 - Dec 17
includes taxes & fees
Book a stay at this business-friendly aparthotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stefanie H. Weill Center for the Performing Arts and Above & Beyond Children's Museum are located nearby.
Pool
Breakfast included
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $209 total
Dec 28 - Dec 29
includes taxes & fees
Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
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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.

Best Lodging Options Near Lake Michigan