Woodlawn Vacations from ￥307,376

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Woodlawn Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥382,160, price is now ￥307,376 per person
￥307,376
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Great experience and friendly staff

Reviewed on Apr 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥446,572, price is now ￥335,170 per person
￥335,170
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
This is a gem. The staff were caring, welcoming and accommodating. The property is at a perfect location with many eating and shopping options. The bus stop was feet away and access to the metro a couple blocks away. Breakfast was great; it had a great selection of food. Negative: I tried modifying my reservation a couple weeks prior my stay, after noticing a mistake made at the time of booking. However, I was unable to reach anyone at tye hotel, over the phone. Later, I was told by the site I booked my stay, that the hotel denied the request. I will definitely go back to this hotel!

Reviewed on Apr 5, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was ￥754,171, price is now ￥611,128 per person
￥611,128
per person
May 29 - Jun 1
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
The Thompson Chicago is a wonderful boutique Hotel located in the perfect part of the city.

Reviewed on Apr 6, 2026

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was ￥394,250, price is now ￥329,920 per person
￥329,920
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,503 reviews)
Overall really clean I just wish they had room service, and the TVs had access to Netflix atleast.

Reviewed on Apr 6, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was ￥385,252, price is now ￥323,645 per person
￥323,645
per person
May 14 - May 17
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (3,032 reviews)
A beautiful historic hotel...we very much enjoyed our stay there.

Reviewed on Mar 31, 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

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.

Find hotels in Downtown Chicago

Woodlawn Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥17,301 per night from Apr 16 to Apr 17
￥17,301
￥20,310 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (10,050 reviews)
Great Stay

Reviewed on Apr 6, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,888 per night from Apr 12 to Apr 13
￥21,888
￥25,694 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,071 reviews)
The hotel is perfect. The view was beautiful. Room was clean, staff were professional and friendly. The food and drinks was amazing 😋 😍

Reviewed on Apr 6, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,825 per night from Apr 19 to Apr 20
￥24,825
￥29,142 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,826 reviews)
The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.

Reviewed on Apr 6, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,601 properties in Woodlawn
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 ￥307,376, 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,285
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,348
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,427
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.