Maywood Holidays from £797

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,019, price is now £797 per person
£797
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Amazing view, but basic room

Reviewed on 7 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,082, price is now £813 per person
£813
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on 5 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,018, price is now £1,528 per person
£1,528
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint

Reviewed on 6 Nov 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was £2,673, price is now £2,122 per person
£2,122
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £1,347, price is now £1,074 per person
£1,074
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

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

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 £103 per night from 26 Nov to 27 Nov
£103
26 Nov - 27 Nov
includes taxes & fees
8/10 Very good! (10,115 reviews)
"There is no parking so be prepared and get one of the street parking passes."

Reviewed on 7 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £103 per night from 11 Nov to 12 Nov
£103
11 Nov - 12 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundable
The price is £102 per night from 8 Dec to 9 Dec
£102
8 Dec - 9 Dec
includes taxes & fees
8.8/10 Excellent! (5,592 reviews)
"A little bit old"

Reviewed on 7 Nov 2026

River Hotel
See all 4,907 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
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Maywood attractions

Underground Railroad Memorial at McDonald's

This poignant memorial marks where enslaved people found refuge on the Underground Railway, featuring symbolic broken shackles. Visitors can reflect on this powerful history while viewing the plaque honouring Harriet Tubman.
See properties

What to do in Maywood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Architecture River Tour from Michigan Avenue

Architecture River Tour from Michigan Avenue

£31
per adult
Architecture River Tour from Michigan Avenue
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 £797. 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.