Woodlawn Vacations from NT$91,166

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The Latest Woodlawn Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
Jun 30 - Jul 6
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,022 reviews)
Excellent location!

Reviewed on 2024/5/15

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jun 30 - Jul 6
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on 2024/5/13

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jun 30 - Jul 6
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (679 reviews)
Enjoyed our stay at the Pendry. It is in a great location and very walkable. Housekeeping was great. Enjoyed the restaurant and bar and the staff was very friendly.

Reviewed on 2024/5/15

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Jun 30 - Jul 6
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Location was fantastic and the property is beautiful!

Reviewed on 2024/5/15

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Jun 30 - Jul 6
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
7.8/10 Good! (1,013 reviews)
The bathroom could have been cleaner, the air conditioning barely worked which made the room incredibly hot. The lobby is nice enough, and the staff is super friendly. The location is wonderful.

Reviewed on 2024/5/11

Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago showing a city

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.

Find hotel + flight trips in Downtown Chicago

Woodlawn Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is NT$3,403 per night from May 27 to May 28
NT$3,403
per night
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on 2024/5/14

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is NT$4,784 per night from May 27 to May 28
NT$4,784
per night
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on 2024/5/14

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$7,098 per night from May 27 to May 28
NT$7,098
per night
May 27 - May 28
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on 2024/5/10

The Westin Michigan Avenue Chicago
See all 3,989 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 NT$91,166, 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.

Discover the most popular places to visit in Woodlawn

Image for Jackson Park

Jackson Park

4/5(7 reviews)

Explore the great outdoors at Jackson Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Jackson Park
Image for 63rd Street Beach

63rd Street Beach

Why not spend a lazy afternoon at 63rd Street Beach during your trip to Chicago? Wander the beaches and gardens while you're in the area.

63rd Street Beach
Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.