Des Plaines Vacation Packages
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Your Des Plaines Vacation
Reserve a Des Plaines vacation package that includes everything you need and nothing you don't. Good for cafes, nature and bars and pubs, think about basing yourself in the neighborhood of Rogers Park. If your trip to Des Plaines includes a little sightseeing, don't miss major attractions such as Allstate Arena, Rosemont Theatre and Fashion Outlets of Chicago. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Des Plaines vacation plans into motion!
Top Des Plaines Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,484, price is now CA $1,060 per person
CA $1,060
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,590, price is now CA $1,132 per person
CA $1,132
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Muy bien ubicado, puedes ir caminando por todo el loop y todo esta cerca (si va al downtown), el personal es amable, los cuartos amplios y bonitos, la vista muy bonita (solo que hay edificios al rededor y no ves mas). Los precios de todo en el hotel me parecen un poco elevados.
Reviewed on Apr 15, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,434, price is now CA $1,746 per person
CA $1,746
per person
Jul 6 - Jul 10
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The best hotel I've ever stayed in.
Please get an iron, please get a microwave. And please don’t charge for every single thing! ❤️
Reviewed on Apr 13, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,605, price is now CA $1,942 per person
CA $1,942
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $1,452, price is now CA $1,090 per person
CA $1,090
per person
Jun 27 - Jul 1
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Restaurant next door can be loud and surprise you when entering the lobby. Great location. Will return.
Reviewed on Apr 8, 2026
Des Plaines Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 26 to Apr 27
CA $158
CA $186 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,151 reviews)
Room looked great, basically more like a studio than a hotel room.
Reviewed on Apr 15, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Apr 26 to Apr 27
CA $189
CA $222 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,124 reviews)
Very clean
Reviewed on Apr 15, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CA $213 per night from Apr 27 to Apr 28
CA $213
CA $250 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (5,840 reviews)
Room was hot , we were 6 not enough of towels breakfast good staff were great
Reviewed on Apr 15, 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.
Discover the most popular places to visit in Des Plaines
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Des Plaines
Skydeck - Willis Tower Admission
CA $60
per adult
98% of travellers recommend
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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.
