Downtown Des Plaines Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Jun 27 - Jul 1

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - 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, 2026
    Roundtrip Toronto (YTZ) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YTZNonstop
    CA $1,550
    CA $1,032
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Aug 2 - Aug 7

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (480 reviews)
    "Super nice"
    Reviewed May 20, 2026
    Roundtrip Hamilton (YHM) - Chicago (ORD)
    YHM - ORD1 stop ORD - YYZ1 stop
    CA $2,232
    CA $1,411
    per traveller
    found 17 hours ago
    Level Chicago – Old Town
  • Jul 9 - Jul 12

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,116 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip Toronto (YTZ) - Chicago (ORD)
    YTZ - ORDNonstop ORD - YYZNonstop
    CA $1,614
    CA $1,097
    per traveller
    found 12 hours ago
    Pendry Chicago
  • Jul 28 - Aug 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - 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, 2026
    Roundtrip Edmonton (YEG) - Chicago (ORD)
    YEG - ORD1 stop ORD - YEG1 stop
    CA $2,437
    CA $1,661
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Aug 8 - Aug 12

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,337 reviews)
    "Great location!"
    Reviewed May 23, 2026
    Roundtrip Edmonton (YEG) - Chicago (ORD)
    YEG - ORDNonstop ORD - YEGNonstop
    CA $1,801
    CA $1,286
    per traveller
    found 1 day ago
    Swissotel - Chicago

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 Des Plaines Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
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

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
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

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
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

The Chicago Hotel Collection - Magnificent Mile
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

Things to do

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