Maywood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

    Plan, 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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,023, price is now CA $779 per person
CA $779
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
All the cuteness of a boutique hotel, with all the Marriott amenities and a great staff too! This will be my #1 pick for Chicago hotels from now on

Reviewed on Jul 1, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,393, price is now CA $1,698 per person
CA $1,698
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,720, price is now CA $1,289 per person
CA $1,289
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very close to shopping, eating, and interstate. Great location. We walked to most of what we wanted to do.

Reviewed on Jul 2, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,401 per person
CA $1,401
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
An amazing hotel with an amazing river view! I will definitely be staying there again!

Reviewed on Jul 1, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,067, price is now CA $815 per person
CA $815
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The staff was very friendly and the location was great!

Reviewed on Jul 2, 2026

Ready to book your vacation to Maywood?

 

Choose your dates

Maywood Hotel Deals

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 CA $173 per night from Jul 6 to Jul 7
CA $173
CA $205 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on Jul 2, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $306 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,830 reviews)
"The staff was very friendly and the location was great!"

Reviewed on Jul 2, 2026

Omni Chicago 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 CA $263 per night from Jul 9 to Jul 10
CA $263
CA $312 total
Jul 9 - Jul 10
includes taxes & fees
9/10 Wonderful! (4,480 reviews)
"Excellent location and beautiful hotel"

Reviewed on Jul 2, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,899 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

What to do in Maywood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Maywood

Frequently asked questions

How much does a Maywood vacation package cost?
You'll find cheap prices from CA $779 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.