
Woodlawn Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Woodlawn
Price found within the past 48 hours. Click for updated prices.

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was CA $1,412, price is now CA $990 per person
CA $990
per person
Sep 24 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
I was very impressed with Whitehall hotel there’s nothing I would change about it. My visit was a wonderful visit. Thank you Expedia.
Reviewed on Jul 5, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,057, price is now CA $1,243 per person
CA $1,243
per person
Sep 24 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location.
The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.
Reviewed on Jul 6, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,483, price is now CA $994 per person
CA $994
per person
Sep 24 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Love this hotel , great area
Reviewed on Jul 6, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $2,167, price is now CA $1,473 per person
CA $1,473
per person
Sep 24 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 2026
Where to stay in Woodlawn
Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn

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.
Woodlawn Hotel Deals

Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Jul 9 to Jul 10
CA $240
CA $332 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (1,857 reviews)
"This was a very clean and nice hotel. I enjoyed the room."
Reviewed on Jul 6, 2026

The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jul 27 to Jul 28
CA $233
CA $277 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,695 reviews)
"Tried to use the very small hair dryer only to find out it quite in a puff of black smoke and smelled up the whole room."
Reviewed on Jul 5, 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 8 to Jul 9
CA $172
CA $205 total
Jul 8 - Jul 9
includes taxes & fees
8/10 Very good! (10,179 reviews)
"Broken toilet."
Reviewed on Jul 6, 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 Woodlawn 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.











