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

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 hotel + flight trips 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 Rp1.504.378 per night from 8 Jan to 9 Jan
Rp1.504.378
Rp1.765.990 total
includes taxes & fees
8 Jan - 9 Jan
7.8/10 Good! (8,376 reviews)
"Beautiful area, although not many great food options around. The hotel is pretty outdated, but charming. Also, constant sirens in and around the area…. don’t know how the locals handle it! Although, the transportation is amazingly connected but kinda sketch."

Reviewed on 6 Jan 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp1.652.094 per night from 6 Feb to 7 Feb
Rp1.652.094
Rp1.939.392 total
includes taxes & fees
6 Feb - 7 Feb
8.6/10 Excellent! (3,681 reviews)
"Very nice stuff"

Reviewed on 5 Jan 2025

River Hotel
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 Rp1.750.896 per night from 26 Jan to 27 Jan
Rp1.750.896
Rp2.055.237 total
includes taxes & fees
26 Jan - 27 Jan
8.2/10 Very Good! (3,452 reviews)
Weekend Getaway
"Checkin was quick and smooth Room was clean and nice. Plenty of amenities and restaurants and bars in the area."

Reviewed on 5 Jan 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 3,533 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

Rp615.706
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

Rp789.586
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

Rp550.460
per adult
Color Factory Chicago 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.