Woodlawn Holidays from £955

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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 £1,123, price is now £955 per person
£955
per person
1 Jul - 5 Jul
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy. My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.

Reviewed on 12 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,238, price is now £991 per person
£991
per person
1 Jul - 5 Jul
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!

Reviewed on 13 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,242, price is now £1,041 per person
£1,041
per person
1 Jul - 5 Jul
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location. Very friendly and helpful staff.

Reviewed on 13 May 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,164, price is now £981 per person
£981
per person
1 Jul - 5 Jul
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's

Reviewed on 12 May 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was £1,305, price is now £1,121 per person
£1,121
per person
1 Jul - 5 Jul
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (4,012 reviews)
Very good location near to all the sorrounding.

Reviewed on 15 May 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 £119 per night from 26 May to 27 May
£119
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,121 reviews)
Only thing bad about this is they don’t have parking and parking was $65

Reviewed on 15 May 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £127 per night from 25 May to 26 May
£127
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,175 reviews)
Hotel is a beautiful, smaller boutique property.

Reviewed on 14 May 2026

River 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 £153 per night from 25 May to 26 May
£153
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,146 reviews)
Great location. Comfy bed. Rooftop bar really nice! Friendly service.

Reviewed on 15 May 2026

Hotel Riu Plaza Chicago
See all 4,516 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.
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Frequently asked questions

How much does a Woodlawn travel package cost?
Our Woodlawn travel packages, which start at just £955, 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
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.