Wicker Park Vacation Packages
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Top Holiday Package Deals in Wicker Park
Price found within the past 48 hours. Click for updated prices.
Motel 6 Sycamore, IL
Price was CA $1,239, price is now CA $816 per person
CA $816
per person
Sep 16 - Sep 19
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
7.8/10 Good! (654 reviews)
The bed was shocking comfortable…the room wasn’t “dirty” but it was a stained kind of dirty. I felt it was a little expensive for a Motel 6 but cheaper than the higher end hotels nearby. Staff let me check in slightly early to drop my stuff off for a tournament before our game which was helpful.
Reviewed on Jul 3, 2026
Super 8 by Wyndham Rochelle
Price was CA $1,249, price is now CA $821 per person
CA $821
per person
Sep 16 - Sep 19
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
8.2/10 Very good! (1,000 reviews)
Finding and getting to the breakfast area was a little confusing.
Staff was very helpful.
Reviewed on Jul 2, 2026
AmericInn by Wyndham Woodstock IL
Price was CA $1,296, price is now CA $858 per person
CA $858
per person
Sep 16 - Sep 19
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
8/10 Very good! (1,003 reviews)
Dee at the front. Desk was wonderful. The breakfast left a lot to be desired.
Reviewed on Jul 4, 2026
Where to stay in Wicker Park
Find the best Wicker Park areas and neighborhoods for the activities you enjoy most. Learn more about Wicker Park
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.
Wicker Park 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 $204 per night from Jul 6 to Jul 7
CA $204
CA $243 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very good! (1,685 reviews)
"Everything about this place was amazing 😮💨"
Reviewed on Jul 4, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jul 6 to Jul 7
CA $172
CA $205 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (10,152 reviews)
"Staff was very helpful. The rooms were clean and the historic hotel was really nice. Couldn’t beat the location either."
Reviewed on Jul 4, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
The price is CA $207 per night from Jul 8 to Jul 9
CA $207
CA $293 total
Jul 8 - Jul 9
includes taxes & fees
9.2/10 Wonderful! (1,844 reviews)
"The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!"
Reviewed on Jul 4, 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.
Frequently asked questions
Stay near popular Wicker Park attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
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.