Sawyer Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Sawyer Vacation

Food, history, entertainment and more … There's so much to discover with a Sawyer vacation package. And with the ability to easily customize your city getaway, it's guaranteed to be one that's tough to forget. Fill your schedule with tours of Warren Dunes State Park Beach, Cherry Beach and Round Barn Union Pier Tasting Room, some of the things you simply have to see during a trip to Sawyer. Don't put off exploring this city any longer. The perfect Sawyer vacation is a few clicks away with Expedia.

Top Sawyer Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,794, price is now CA $1,126 per person
CA $1,126
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,165, price is now CA $2,806 per person
CA $2,806
per person
Jan 22 - Jan 25
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 2026

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 CA $1,820, price is now CA $1,271 per person
CA $1,271
per person
Jan 22 - Jan 25
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
We had an easy check in & check out. We had an amazing view from our room. It was quiet, the food on site was good. We do wish check out was later then noon!! We will be back again to stay. Lirica restaurant had good food the breakfast was on point. Definitely loved the mocktails!!Offshore food was great service was excellent. Bar Sol Maricos food was delicious. On two different days drinks such as lemonade and tea tasted water down we did let the waitress know but we were still charged. I recommend the food and soda.

Reviewed on Nov 15, 2026

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Sawyer Hotel Deals

Quality Inn Sawyer

Quality Inn Sawyer

2.5 out of 5
12850 Super Dr Sawyer MI
Fully refundable
The price is CA $90 per night from Nov 23 to Nov 24
CA $90
CA $95 total
Nov 23 - Nov 24
includes taxes & fees
Quality Inn Sawyer
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

Sawyer MI
10/10 Exceptional! (48 reviews)
"The Sawyer House is an ideal location for a family reunion! We gathered five couples for a long weekend of games, home cooking, long walks, and football, and the house accommodated our needs for comfort, privacy, and space. The hot tub and outdoor fire pit were highlights, and we could see how a ..."

Reviewed on Nov 10, 2026

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Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn
7 Bedroom Country Estate with Large Private Pool!

7 Bedroom Country Estate with Large Private Pool!

Sawyer MI
10/10 Exceptional! (50 reviews)
"We rented this home for a 40th birthday celebration and it did not disappoint. The home was so clean and beautiful and had everything you would need. The host was very responsive and answered all of our questions. We would absolutely come back!"

Reviewed on Sep 14, 2026

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7 Bedroom Country Estate with Large Private Pool!
See all 2,171 properties in Sawyer
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.
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Stay near popular Sawyer attractions

Warren Dunes State Park Beach

9.2/10 (58 reviews)
Why not spend a lazy afternoon at Warren Dunes State Park Beach during your trip to Sawyer? Stroll along the area's beaches or simply enjoy its breweries.
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Frequently asked questions

How much does a Sawyer vacation package cost?
Offering excellent value package deals from CA $1,126 on Expedia, you'll be surprised at how little a vacation to Sawyer costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Sawyer?
If you're looking to snag a cheap Sawyer vacation package, consider planning a trip in April, November and December. You're likely to find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Sawyer?
Generally, a handful of days is ideal for a Sawyer vacation. With a well-organized itinerary, you can see all the main sights including Cherry Beach, as well as explore some hidden gems along the way.
How to find the best Sawyer package deals?
Use Expedia's filter tool to find some tempting Sawyer package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Sawyer package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Sawyer vacation as a package?
You can enjoy significant savings on your Sawyer retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Sawyer?
If you're planning an impromptu Sawyer trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Sawyer?

  1. Choose your travel dates: What you want to do in Sawyer and your favourite season will help you decide when to get away.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to experiences and flights. Your hotel will likely be the largest expense during your trip to Sawyer.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Sawyer. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the right Sawyer vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.