Maywood Vacation Packages

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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.
Staybridge Suites Chicago-Oakbrook Terrace by IHG

Staybridge Suites Chicago-Oakbrook Terrace by IHG

3 out of 5
York Center
Price was CA $948, price is now CA $748 per person
CA $748
per person
Mar 28 - Apr 4
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,000 reviews)
Breakfast was good. Separate bedroom and living room. Kitchen with stove and basic utensils with dishwasher. Renovation of the property is in progress hope to see some improved quality of beds and stove with increased in-premise Parking slots for all guests. Overall had a pleasant stay.

Reviewed on Feb 16, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,340, price is now CA $1,610 per person
CA $1,610
per person
May 14 - May 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $1,831, price is now CA $1,348 per person
CA $1,348
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,326, price is now CA $996 per person
CA $996
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The room was excellent

Reviewed on Feb 16, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,081, price is now CA $835 per person
CA $835
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend.

Reviewed on Feb 15, 2026

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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 $122 per night from Feb 18 to Feb 19
CA $122
CA $143 total
Feb 18 - Feb 19
includes taxes & fees
8/10 Very Good! (9,872 reviews)
Room was nice and clean. Hotel had a fantastic classic look and feel. Perfect place to stay for shows at the Auditorium theater across the street. It's a very old building so the heating and hot water situation is a little off compared to newer hotels but nothing that would deter me from staying ...

Reviewed on Feb 13, 2026

Congress Plaza 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 CA $154 per night from Mar 4 to Mar 5
CA $154
CA $219 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,355 reviews)
The room was excellent

Reviewed on Feb 16, 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Feb 27 to Feb 28
CA $189
CA $261 total
Feb 27 - Feb 28
includes taxes & fees
8.4/10 Very Good! (2,618 reviews)
It was great

Reviewed on Feb 12, 2026

Hilton Chicago
See all 5,181 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

Discover the most popular places to visit in Maywood

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy 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 featuring a sunset and rides

Navy Pier

4.5/5(459 reviews)

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

Navy Pier

What to do in Maywood

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Maywood

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