Downtown Skokie Vacation Packages
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Top Holiday Package Deals in Downtown Skokie
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $798, price is now CA $598 per person
CA $598
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on Jul 11, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,141, price is now CA $2,140 per person
CA $2,140
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $784, price is now CA $605 per person
CA $605
per person
Aug 11 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Great hotel with perfect and safe location. I loved the suite room with separate coach very roomy! The staff are the best, and the breakfast is great. Highly recommend this hotel!
Reviewed on Jul 12, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was CA $1,264, price is now CA $977 per person
CA $977
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $974, price is now CA $753 per person
CA $753
per person
Aug 11 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026
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
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,735 reviews)
"Great location, clean, and a super breakfast!"
Reviewed on Jul 11, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
The price is CA $316 per night from Jul 26 to Jul 27
CA $316
CA $422 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,909 reviews)
"Great hotel with perfect and safe location. I loved the suite room with separate coach very roomy! The staff are the best, and the breakfast is great. Highly recommend this hotel!"
Reviewed on Jul 12, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Aug 10 to Aug 11
CA $268
CA $318 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very good! (10,232 reviews)
"Great value for the price"
Reviewed on Jul 12, 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.
Stay near popular Downtown Skokie attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.