Fair Plain Vacation Packages
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Your Fair Plain Vacation
Our Fair Plain vacation packages let you create your own adventure. Tailor your getaway to your interests and needs and make the most of your time in this fantastic city. Fill your schedule with tours of Silver Beach, Harbor Shores Golf Club and Lake Michigan College, some of the things you just have to see during a trip to Fair Plain. Expedia has what you need to escape your routine. Tailor your vacation to Fair Plain to suit your style of travel, whatever that may look like.
Top Fair Plain Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,430, price is now CA $1,028 per person
CA $1,028
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,156 reviews)
We had reserved a king bed, but since we checked in later in the evening, I guess none were available and my wife and I ended up with twin beds instead. Overall, our experience with the front desk staff was mixed — some were very friendly and helpful, while others were not.
Reviewed on May 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,936, price is now CA $1,288 per person
CA $1,288
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on May 28, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,983, price is now CA $1,403 per person
CA $1,403
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,466, price is now CA $1,064 per person
CA $1,064
per person
Jun 30 - Jul 4
just found
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (117 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 2026
Fair Plain Hotel Deals
Howard Johnson by Wyndham Benton Harbor/St. Joseph
798 Ferguson Dr Benton Harbor MI
4.6/10 (1,000 reviews)
"The room is clean the staff was polite the parking was convenient and it is family-friendly but they did not have no coffees in the room and they did not have the restaurant open so you could get coffee and they did not offer any coffee to their guest"
Reviewed on May 28, 2026
The 1888 House-Beach Town Luxury
Benton Harbor MI
The price is CA $285 per night from Jun 4 to Jun 5
CA $285
CA $509 total
Jun 4 - Jun 5
includes taxes & fees
9.4/10 Exceptional! (9 reviews)
"We had a great weekend. Place was clean and host was very quick to respond."
Reviewed on Nov 30, 2025
Napier House-Romantic Private Luxury mins to Beach
Benton Harbor MI
The price is CA $288 per night from Jun 1 to Jun 2
CA $288
CA $512 total
Jun 1 - Jun 2
includes taxes & fees
8.6/10 Excellent! (14 reviews)
"i enjoyed this home soo much very nice & comfortable just like homeeee from the house soo clean smelling good everything was perfect will definitely will coming back!"
Reviewed on Mar 30, 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.
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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.
