Woodlawn Vacations from ￥266,162
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The Latest Woodlawn Vacation Packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
￥284,026
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Needed a quick hotel. The room is very cutest, very clean, and calming. They have a bar downstairs, if you're into that and offer loose leaf tea + coffee in the lobby, staff is pretty helpful. Breakfast is not free / complientary.
It's $30 extra, so plan ahead if that's important to you. Room is cute and clean, overall. And the building easy to find.
Reviewed on Sep 6, 2026
Four Seasons Hotel Chicago
Downtown Chicago
￥358,164
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥271,980
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
The views from the hotel were breathtakingly beautiful. The food, the shops, restaurants, entertainment, etc. on the premises were Top Tier. I highly recommend this stay!
Reviewed on Sep 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
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.
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.
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.
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
￥17,333
￥20,607 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,298 reviews)
"The hotel was nicely maintained. My only issue was that the beds are hard as a rock. The pillows are great. The bathroom door kept sticking, because they put too many coats of paint on it. It was updated nicely."
Reviewed on Sep 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥26,560
￥31,577 total
Oct 6 - Oct 7
includes taxes & fees
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"
Reviewed on Sep 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
How much does a Woodlawn vacation package cost?
Our Woodlawn packages, which start at just ￥266,162, 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 acclaimed art scene in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥6,484
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.