Maywood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Maywood Vacation
With a Maywood vacation 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 Center 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 vacation is just a few clicks away with Expedia.
Top Maywood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
CA $818
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay.
Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that.
Overall a great spot. Affordable and lots of space with great views!
Reviewed on Aug 15, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,132
per person
Oct 22 - Oct 25
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,501
per person
Oct 19 - Oct 23
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
CA $1,843
per person
Oct 11 - Oct 15
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
Broken elevator causing long lines and delays. Coffee set up in the lobby was awkward and $4 for a cup. Friends found bed bug in their bed. Staff very nice and good location.
Reviewed on Aug 16, 2026
Ready to book your vacation to Maywood?
Maywood Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $173
CA $205 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (2,016 reviews)
"It bc was good"
Reviewed on Aug 16, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $338
CA $397 total
Sep 12 - Sep 13
includes taxes & fees
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.
Stay near popular Maywood attractions
Underground Railroad Memorial at McDonald's
You can find out about the history of Maywood with a visit to Underground Railroad Memorial at McDonald's. Discover the area's festivals and shops.
What to do in Maywood
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Maywood vacation package cost?
You'll find cheap prices from CA $818 on Expedia for your Maywood getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Maywood costs.
What are the cheapest months to go to Maywood?
The off-season is the best time to head to Maywood if you're trying to save. Another tip for finding cheap Maywood vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Maywood?
We recommend planning a Maywood vacation for a minimum of 6 days. This will give you plenty of time to check off key attractions including Harlem Irving Plaza and Unity Temple, and also check out neighbourhoods like North Riverside and Galewood. You might even be able to make time for one or two day trips from Maywood.
How to find the best Maywood package deals?
Begin your search for a Maywood package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Maywood package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Maywood escape off to a flying start.
Is it cheaper to book a Maywood vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Maywood vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Maywood?
Land incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Maywood escape.
How to plan a trip to Maywood?
- Choose when to get away: Check your calendar and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Maywood.
- Figure out your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Maywood.
- Decide your trip length: Consider how long you want to spend exploring Maywood. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Maywood vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
