Woodlawn Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Plan, book, travel with confidence
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    Better together
    Save up to NT$5,755 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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

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 NT$5,697 per night from Jun 5 to Jun 6
NT$5,697
per night
Jun 5 - Jun 6
7.6/10 Good! (6,812 reviews)
"No hot water during whole stay. Had to shower in a fellow traveller's room."

Reviewed on 2024/5/27

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is NT$6,662 per night from Jun 17 to Jun 18
NT$6,662
per night
Jun 17 - Jun 18
8.6/10 Excellent! (2,911 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."

Reviewed on 2024/5/28

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$6,435 per night from Jun 16 to Jun 17
NT$6,435
per night
Jun 16 - Jun 17
8.4/10 Very Good! (1,975 reviews)
"I loved the service we got. Would recommend staying here!"

Reviewed on 2024/5/28

Eurostars Magnificent Mile
See all 3,980 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 , 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

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Jackson Park

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
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Wrigley Field

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.