Woodlawn Holidays

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Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago featuring 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 hotels in Downtown Chicago

Top hotels in Woodlawn

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 Rp1.395.984 per night from 17 Feb to 18 Feb
Rp1.395.984
Rp1.638.745 total
includes taxes & fees
17 Feb - 18 Feb
7.8/10 Good! (8,463 reviews)
"It’s always nice at the congress."

Reviewed on 5 Feb 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp2.264.727 per night from 12 Feb to 13 Feb
Rp2.264.727
Rp2.658.564 total
includes taxes & fees
12 Feb - 13 Feb
9.6/10 Exceptional! (1,597 reviews)
"Awesome, customer service."

Reviewed on 5 Feb 2025

L7 Chicago by LOTTE
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp1.629.300 per night from 13 Feb to 14 Feb
Rp1.629.300
Rp1.912.635 total
includes taxes & fees
13 Feb - 14 Feb
9.2/10 Wonderful! (2,642 reviews)
"The property is nice just didn’t like how the terrace was not open"

Reviewed on 5 Feb 2025

citizenM Chicago Downtown
See all 4,108 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 holiday package cost?
Our Woodlawn packages, which start at just , are the best way to save. Pick your favourite 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 holiday 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 holiday you’ve always dreamed of in Woodlawn is closer than you thought!
Where should I stay in Woodlawn?
Most travellers 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 holiday?
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 holiday package lets you organise your escape your way. Plus, you’ll get access to great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the more you’ll save!
Can I choose my airline with a Woodlawn Expedia holiday 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 holiday.
If I'm not able to travel, can I cancel my Woodlawn holiday package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel or change your Woodlawn holiday 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.

Popular places to visit

Lorado Taft's Midway Studios

You can find out about the history of Chicago when you stop by Lorado Taft's Midway Studios. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Lorado Taft's Midway Studios

Things to do

Flyover in Chicago

Flyover in Chicago

Rp615.021
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

Rp788.708
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

Rp719.654
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.