Woodlawn Holidays from £1,140

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Your Woodlawn Holiday

Book a customized holiday package to Woodlawn and get set to experience its cycling, golfing and walking. However you want to spend your getaway in this green neighbourhood, there are plenty of opportunities for both adventure and relaxation. Some nearby attractions to visit during your trip to Woodlawn include University of Chicago, Chicago Museum of Science and Industry and Robie House. Whatever your ideal Woodlawn holiday may look like, you can make it a reality with Expedia.

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 £1,517, price is now £1,140 per person
£1,140
per person
2 May - 9 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!

Reviewed on 29 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,387, price is now £1,516 per person
£1,516
per person
2 May - 9 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location. Clean, comfortable, friendly staff.

Reviewed on 30 Mar 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,682, price is now £1,816 per person
£1,816
per person
30 May - 6 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon

Reviewed on 29 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,414, price is now £1,722 per person
£1,722
per person
30 May - 6 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel offered many amenities including gym, sauna, dining on the ground level and effective housekeeping. The hotel was walking distance to many nearby restaurants and activities.

Reviewed on 30 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,860, price is now £2,099 per person
£2,099
per person
2 May - 9 May
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality

Reviewed on 29 Mar 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 £102 per night from 5 Apr to 6 Apr
£102
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (10,019 reviews)
The room is small (two full beds). We had a big bug in the bathroom on the third night. The hotel has a run-down feel, the lobby is not well staffed and the gift shop and hotel restaurants are deserted or not open. Other than the lake view, I found little good things to say about the hotel. I sent ...

Reviewed on 30 Mar 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 £108 per night from 7 Apr to 8 Apr
£108
7 Apr - 8 Apr
includes taxes & fees
9/10 Wonderful! (4,024 reviews)
Clean room, helpful staff, would stay again

Reviewed on 30 Mar 2026

Hilton Chicago/Magnificent Mile Suites
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 £128 per night from 12 Apr to 13 Apr
£128
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (5,804 reviews)
Evening snacks/drinks were great, as was breakfast. Rooms were clean. Staff was great. It was hot and wouldnt get cool enough anywhere. The pool was too crowded to enjoy but we were happy with our stay overall!

Reviewed on 30 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,502 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
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Woodlawn travel package cost?
Our Woodlawn travel packages, which start at just £1,140, are the perfect way to save big. Select your favourite hotels, flights and rental car to create your dream escape.
If I'm not able to travel, can I cancel my Woodlawn travel package?
Yes you can, and we're here to help. You may be able to change or cancel your Woodlawn travel package at no cost within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for further information.
How do I get a cheap travel package to Woodlawn?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you money too. A Woodlawn travel package makes it easy to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your busy schedule won't be a problem. Not only that, we've got over 1,000,000 properties globally to choose from. Now that's what we call choice. Whatever your budget, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Woodlawn holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan from Klarna.

Where should I stay in Woodlawn?
A trip to Woodlawn isn't complete until you've seen Millennium Park and Wrigley Field. Stay somewhere within walking distance for easy access to these popular attractions.
What are the top hotels in Woodlawn?
Book a stay at Hyatt Regency Chicago. It's one of this area's most sought-after hotels. Another well-known option in Woodlawn is The Godfrey Hotel Chicago.
How far in advance should I book my Woodlawn holiday?
It's always wise to book early. Airlines generally release flights nearly 12 months in advance, and this is when you can land some of the cheapest prices. Just been told you need to take your holiday time in a few weeks? That's alright! Expedia are never short on fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Woodlawn travel package include?
Select from a combination of rental cars, flights and hotels. Once you've made your booking, you can add activities and tours. Want to pick your fare class? That's easily done too. The choice is yours when it comes to crafting your dream Woodlawn escape.
What should I know before booking a Woodlawn travel package?
So many places to explore, so many things to do. With a package, you'll be able to cross more of them off your list. Combine your flights, rental cars and hotels and get set to save.
Can I choose my airline with a Woodlawn Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our travel packages give you the freedom to pick from available flights, hotels and activities that fit your needs.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£29
per adult
98% of travellers recommend
Flyover in 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. Flight-inclusive packages are ATOL protected.