Woodlawn Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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

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

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 Rp2.488.540 per night from 29 Jun to 30 Jun
Rp2.488.540
Rp2.958.625 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,164 reviews)
"The location was excellent. Close to all the museums, shopping district and river walk."

Reviewed on 3 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is Rp2.711.492 per night from 28 Jun to 29 Jun
Rp2.711.492
Rp3.223.692 total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,509 reviews)
"Clean room"

Reviewed on 3 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp3.395.905 per night from 30 Jun to 1 Jul
Rp3.395.905
Rp4.549.451 total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,330 reviews)
"Great rooftop bar and breakfast."

Reviewed on 3 Jun 2026

Hotel Riu Plaza Chicago
See all 4,496 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp479.088
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

Rp733.892
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.934.096
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.