Woodlawn Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,785, price is now €1,273 per person
€1,273
per person
26 Jul - 31 Jul
found 10 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk. Room smelled bad, dirty carpet.

Reviewed on 24 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,960, price is now €2,051 per person
€2,051
per person
26 Jul - 31 Jul
found 10 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo

Reviewed on 23 Jun 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,178, price is now €1,560 per person
€1,560
per person
26 Jul - 31 Jul
found 10 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Great location, great space in the rooms!!

Reviewed on 21 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €3,025, price is now €2,181 per person
€2,181
per person
26 Jul - 31 Jul
found 10 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.

Reviewed on 24 Jun 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €3,435, price is now €2,554 per person
€2,554
per person
26 Jul - 31 Jul
found 10 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.

Reviewed on 21 Jun 2026

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 €142 per night from 29 Jun to 30 Jun
€142
29 Jun - 30 Jun
includes taxes & fees
8/10 Very good! (10,187 reviews)
"Our room was spacious and clean. Everything works and soundproofing was great in a busy hotel. The only could make it better would be adding a door to the main bedroom and slightly larger TV (or just completely get rid of it)."

Reviewed on 25 Jun 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is €154 per night from 2 Jul to 3 Jul
€154
2 Jul - 3 Jul
includes taxes & fees
9/10 Wonderful! (4,456 reviews)
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."

Reviewed on 24 Jun 2026

Hilton Chicago/Magnificent Mile Suites
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 €213 per night from 5 Jul to 6 Jul
€213
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (4,529 reviews)
"Très bel hôtel bien situé dans un beau quartier ! Excellent rapport qualité-prix. Chambre un peu petite mais confortable! Très beau déjeuner de type buffet et très belle terrasse sur le toit mais menu limité."

Reviewed on 25 Jun 2026

Hotel Riu Plaza Chicago
See all 4,560 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 €1,273, 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 theatre scene in this vibrant area.

Lorado Taft's Midway Studios

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€34
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.