Downtown Skokie Vacation Packages
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- Level Chicago Fulton Market
Jun 27 - Jul 1Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (485 reviews)"Perfect stay"Reviewed May 20, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,457CA $975found 1 day agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jun 27 - Jul 1Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (2,508 reviews)"The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay."Reviewed May 20, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,870CA $1,271found 1 day agoper traveller - Pendry Chicago
Jul 23 - Jul 26Pendry Chicago + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (1,126 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 - YTZ • NonstopCA $1,763CA $1,251found 1 day agoper traveller - Trump International Hotel & Tower Chicago
Jun 27 - Jul 1Trump International Hotel & Tower Chicago + Flight
Downtown Chicago4 nights9.6/10 - Exceptional (1,875 reviews)"Great experience! Would stay here agin"Reviewed May 18, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $2,513CA $1,789found 1 day agoper traveller - Level Chicago - River North
Jul 10 - Jul 14Level Chicago - River North + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (1,020 reviews)"Great experience and shoutout to the front desk people when I checked in ! They were very accommodating and kind . "Reviewed May 20, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,678CA $1,200found 1 day agoper traveller
Where to stay in Downtown Skokie
Find the best Downtown Skokie areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Skokie
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 Skokie Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good for a sleep and go. Not horrible, certainly not the best hotel i've ever stayed at."
Reviewed on May 20, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,201 reviews)
"Breakfast bar was very good just need 0to go cups for coffee.I'm"
Reviewed on May 21, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,447 reviews)
"great location and spacious room. good value"
Reviewed on May 21, 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 Skokie
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.