Downtown Des Plaines Vacation Packages
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- The Talbott, Autograph Collection
Jun 27 - Jul 1The Talbott, Autograph Collection + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (116 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 May 17, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,550CA $1,032found 1 day agoper traveller - Level Chicago – Old Town
Aug 2 - Aug 7Level Chicago – Old Town + Flight
Downtown Chicago5 nights9.0/10 - Wonderful (480 reviews)"Super nice"Reviewed May 20, 2026Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YYZ • 1 stopCA $2,232CA $1,411found 17 hours agoper traveller - Pendry Chicago
Jul 9 - Jul 12Pendry Chicago + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (1,116 reviews)"Great staff and perfect place to be in the middle of everything!"Reviewed April 27, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,614CA $1,097found 12 hours agoper traveller - Level Chicago Fulton Market
Jul 28 - Aug 1Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (488 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 May 22, 2026Roundtrip • Edmonton (YEG) - Chicago (ORD)YEG - ORD • 1 stop ORD - YEG • 1 stopCA $2,437CA $1,661found 1 day agoper traveller - Swissotel - Chicago
Aug 8 - Aug 12Swissotel - Chicago + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (3,337 reviews)"Great location!"Reviewed May 23, 2026Roundtrip • Edmonton (YEG) - Chicago (ORD)YEG - ORD • Nonstop ORD - YEG • NonstopCA $1,801CA $1,286found 1 day agoper traveller
Where to stay in Downtown Des Plaines
Find the best Downtown Des Plaines areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Des Plaines
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Downtown Des Plaines Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from May 25 to May 26
CA $185
CA $219 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."
Reviewed on May 23, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $330 per night from Jun 16 to Jun 17
CA $330
CA $432 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,221 reviews)
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."
Reviewed on May 24, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $178 per night from May 27 to May 28
CA $178
CA $212 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,464 reviews)
"There're bed bugs. Be careful"
Reviewed on May 24, 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 Downtown Des Plaines
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
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
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.