Woodlawn Holidays

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Your Woodlawn Holiday

From its cycling to its golfing and walking, there are tons of convincing reasons to book a holiday package to Woodlawn. When you're ready to escape the everyday, this green neighbourhood is calling. Wondering what to see and do during your trip to Woodlawn? Nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Robie House are good places to begin. Expedia will help put your plans into action. Book your perfect Woodlawn holiday now.

Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jun 24 - Jun 28

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (487 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,371
    AU$3,762
    per traveller
    found 20 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jun 24 - Jun 28

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,877 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,435
    AU$4,637
    per traveller
    found 20 hours ago
    Trump International Hotel & Tower Chicago
  • Seasonal outdoor pool, pool loungers
    Jun 24 - Jun 28

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,231 reviews)
    "We had an incredible stay here. The room was very nice as we stayed in a junior suite so the extra charge was definitely worth it. You’re on the 17th floor and you’re able to have a good view of the city. You also are one floor away from the rooftop restaurant and bar. The decor and aesthetics in the hotel are top-notch. Definitely picture worthy. Definitely walkable and it’s less than quarter mile from the hotel to the lake. 10 out of 10 definitely recommend."
    Reviewed May 23, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,114
    AU$4,381
    per traveller
    found 20 hours ago
    Viceroy Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Jun 24 - Jun 28

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,721 reviews)
    "Great location!"
    Reviewed May 22, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,627
    AU$3,997
    per traveller
    found 20 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Meeting facility
    Jun 24 - Jun 28

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,366 reviews)
    "Great location"
    Reviewed May 19, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,788
    AU$4,193
    per traveller
    found 20 hours ago
    Thompson Chicago, by Hyatt

Our guide on 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

Our pick of the best 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 AU$223 per night from 25 May to 26 May
AU$223
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,133 reviews)
"400 dollars not worth it period"

Reviewed on 23 May 2026

Congress Plaza Hotel
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 AU$305 per night from 27 May to 28 May
AU$305
27 May - 28 May
includes taxes & fees
Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 25 May to 26 May
AU$202
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,458 reviews)
"Hotel was very clean, staff very helpful, bar and rooftop staff was great."

Reviewed on 23 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,546 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.
All Inclusive Holidays
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Beach Holidays
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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.

Discover the most popular places to visit in Woodlawn

613-28 Japanese Island Jackson Park Chicago

Jackson Park

Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Jackson Park

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
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.