Maywood Holidays from £612

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Your Maywood Holiday

With a Maywood holiday package, say goodbye to endless planning and hello to stress-free adventure. Every detail of your getaway has been taken care of before you depart, so you can make the most of your time experiencing this exciting city. Fill your itinerary with visits to Brookfield Zoo, Oakbrook Centre Mall and Frank Lloyd Wright Historic District, some of the attractions you shouldn't miss during a trip to Maywood. Whoever you're taking time off with and whatever you plan to spend, your dream Maywood holiday is just a few clicks away with Expedia.

Top Maywood Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £972, price is now £612 per person
£612
per person
8 Nov - 13 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
I enjoyed my stay here

Reviewed on 23 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,400, price is now £838 per person
£838
per person
8 Nov - 13 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,738, price is now £1,078 per person
£1,078
per person
8 Nov - 13 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,683, price is now £1,074 per person
£1,074
per person
8 Oct - 12 Oct
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊

Reviewed on 24 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,086, price is now £1,365 per person
£1,365
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.

Reviewed on 23 Aug 2025

Maywood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
24,000
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago

Top hotels in Maywood

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 1 Sept to 2 Sept
£131
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug 2025

The Wade
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 £94 per night from 26 Aug to 27 Aug
£94
26 Aug - 27 Aug
includes taxes & fees
7.8/10 Good! (8,995 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on 23 Aug 2025

Congress Plaza Hotel
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 £132 per night from 3 Sept to 4 Sept
£132
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on 23 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,075 properties in Maywood
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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Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Maywood

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
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 Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Maywood

Frequently asked questions

How much does a Maywood travel package cost?
Get set to book, because a trip to Maywood starts from just £612. When you bundle your flights, hotels and more into a travel package, you'll land the biggest bargains.
If I'm not able to travel, can I cancel my Maywood travel package?
You can cancel your Maywood booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Maywood?
Bundle your hotel and flight bookings, add on extras such as a rental car or activities, and save with a Maywood travel package. You won't just land big discounts on your escape — you'll have loads of choice at your fingertips too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 properties globally. Your dream holiday starts right here, right now!
Does Expedia offer Book Now, Pay Later Maywood holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan that works for you during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your flights, hotel and car hire with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying small amounts each month works for you, pick this option at checkout.
  • Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan from Klarna.

Where should I stay in Maywood?
With so much to do in Maywood, it's a good idea to lock in a hotel near its attractions. Ernest Hemingway Museum and House, Oak Park Conservatory and Unity Temple are some top ones to put on your must-see list.
What are the top hotels in Maywood?
Book a room at Hyatt Regency Chicago. It's one of this area's most popular properties. Another top option in Maywood is The Godfrey Hotel Chicago.
How far in advance should I book my Maywood holiday?
It depends on the airline, but you can normally browse through international flights on Expedia nearly a year in advance. While it's generally recommended to book ahead of time, lucky customers will sometimes nab a cheaper ticket only weeks before departure dates.
What does an Expedia Maywood travel package include?
Travel packages include flights, hotels and rental cars, but you can mix and match them to create your perfect Maywood trip. You can also add on tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll get access to discounts you won't find elsewhere.
What should I know before booking a Maywood travel package?
Whether it's adventure or relaxation you're seeking, a Maywood travel package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Maywood Expedia travel package?
You can. Expedia has access to more than 550 partner airlines all over the world, so choose the carrier that suits your budget needs.

* 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.