Woodlawn Vacation Packages
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Top Holiday Package Deals in Woodlawn
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $988
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Great hotel in the perfect location as everything is walking distance. Rooms are very clean and comfortable. Breakfast buffet is great. Only issue i had with the stay was the rooftop bar. Thought this was going to be a great spot to overlook the city but the view was average. Service at the bar was very poor. Went there a couple times with the first time we didnt get a server to come to our table for the first 15-20 mins of being there so I had to walk up to the bar to get my own drink. The second time we sat at a table and server took our drink orders but after 20 minutes of waiting for my drink to come out i had to speak with a manager. The manager was great at that point and was very apologetic and comped our drinks. Overall this was great stay but was very expensive 4 day trip.
Reviewed on Oct 5, 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
4 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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Woodlawn Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $165
CA $197 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very good! (10,183 reviews)
"Clean, comfortable, easy checkin and out. Room service dinner didnt get order correct but did refund missing items. Great location. Bathroom door creaked, heard the neighbours clearly.. no parking and closest was the lot behind hotel, $65/day, not secure at all. Would stay again if i didnt have an ..."
Reviewed on Oct 5, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $229
CA $272 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (5,491 reviews)
"We loved it"
Reviewed on Oct 5, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $204
CA $242 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (2,418 reviews)
"The staff was just blatantly unhelpful. The front desk was often unmanned and could not take requests whether it was for a checkout or to ask about how a food delivery had been misplaced. I’ve seen HolidayInns with better customer service."
Reviewed on Oct 5, 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
How much does a Woodlawn vacation package cost?
Our Woodlawn packages, which start at just CA $864, are the best way to save. Pick your favorite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Woodlawn?
Bundle your hotels and flights with Expedia to save on your next exciting adventure. With over 550 partner airlines and 1,000,000 hotel options worldwide, your Woodlawn vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not throw in a few exciting tours and activities? It's an easy way to unlock even more savings. That vacation you've always dreamed of in Woodlawn is closer than you thought!
Where should I stay in Woodlawn?
Most travelers who visit Woodlawn include University of Chicago and Chicago Museum of Science and Industry on their bucket lists. Why not choose a hotel that's close to these fantastic attractions?
How far in advance should I book my Woodlawn vacation?
Browse Expedia to compare international airfares as early as possible. You can generally purchase a ticket up to 12 months prior to departure. If you don't see your preferred carrier, or you've left things to the last minute, fear not. Low prices to Woodlawn sometimes appear just weeks before the date of departure.
What does an Expedia Woodlawn travel package include?
Flights, hotels and rental cars — we have them well covered. With Expedia, you can create your Woodlawn package however you want. All you have to do is figure out just what you need. Once you've made your booking, you can add extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Woodlawn travel package?
Whether it's relaxation or adventure you're after, a Woodlawn vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Woodlawn Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you sure can! Simply choose your preferred air carrier and create your ideal Woodlawn vacation.
If I'm not able to travel, can I cancel my Woodlawn vacation package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Woodlawn vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, visit our Customer Service Portal for more information.
Stay near popular Woodlawn attractions
Jackson Park
7.4/10 (9 reviews)
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.
Obama Presidential Center
You can spend an afternoon exploring the galleries in Obama Presidential Center during your trip to Chicago. Wander the beaches and gardens while you're in the area.
Rubenstein Forum
Learn about the events happening at Rubenstein Forum during your trip to Chicago. Amble around the area's beaches or visit its shops.
Jackson Park Driving Range
You can take time to visit Jackson Park Driving Range during your travels to Chicago. Make time to visit the shops and churches while you're in the area.
Bob-O-Link Meadow
Enjoy an outing to Bob-O-Link Meadow during your stay in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Things to do
Wendella's Lake and River Architecture Tour
CA $63
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.