Woodlawn Holidays
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The Latest Woodlawn Holiday Packages
- Hotel Felix River North/Magnificent Mile
17 Dec - 21 DecHotel Felix River North/Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.4/10 - Very good (3,175 reviews)"The location is in a great area , you can’t beat it honestly. For the price and where you are, it was worth it. The staff was helpful as well. However, if you’re looking for a luxury stay, you may want to look else."Reviewed November 9, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€913€785found 13 hours agoper traveller - Swissotel - Chicago
17 Dec - 21 DecSwissotel - Chicago + Flight
Downtown Chicago4 nights4.5 star property9.0/10 - Wonderful (3,584 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,139€931found 13 hours agoper traveller - LondonHouse Chicago, Curio Collection by Hilton
17 Dec - 21 DecLondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights4.5 star property9.4/10 - Exceptional (3,902 reviews)"Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile...."Reviewed November 9, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,172€968found 13 hours agoper traveller - The Talbott, Autograph Collection
17 Dec - 21 DecThe Talbott, Autograph Collection + Flight
Downtown Chicago4 nights4.5 star property9.4/10 - Exceptional (196 reviews)"I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure."Reviewed November 8, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€1,046€864found 13 hours agoper traveller - Hotel Saint Clair- Magnificent Mile
17 Dec - 21 DecHotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (2,396 reviews)"The rooms were clean,but small. The hotel staff were very friendly and helpful. I would stay here again"Reviewed November 10, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct€986€827found 13 hours agoper traveller
Where to stay in Woodlawn
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Discover the most popular places to visit in Woodlawn
What to do near Woodlawn
Architecture River Tour from Michigan Avenue
Woodlawn Hotel Deals
"Incredible hotel n gorgeous lake view. Staff were so friendly and helpful. Loved it. Will stay here again for sure!"
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton"Great"
Best Western Grant Park Hotel
Best Western Grant Park Hotel
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop"The room was clean. There was only 1 working elevator which was annoying to wait for every time. Other than that everything was good."
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Every thing is good!👍🌹"
Frequently Asked Questions
How much does a Woodlawn holiday package cost?
Our Woodlawn packages, which start at just €785, 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.