Homewood Vacation Packages

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Your Homewood Vacation

Come and discover this interesting city for yourself with a Homewood vacation package. Think about basing yourself in the neighborhood of South Deering, which is good for golfing and nature, and your time here is bound to be unforgettable. A trip to Homewood is an excellent opportunity to do a bit of sightseeing. Be sure to look around popular attractions like Hollywood Casino Amphitheatre, Coyote Run Golf Course and River Oaks Center. Your Homewood vacation is a few clicks away. Browse airfares, hotels and more on Expedia for a getaway that's tailored to suit your travel style.

Top Homewood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,457, price is now CA $975 per person
CA $975
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (477 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $3,626, price is now CA $1,987 per person
CA $1,987
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
Very good Outstanding service

Reviewed on May 19, 2026

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 CA $2,965, price is now CA $1,891 per person
CA $1,891
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
I loved it here and will definitely stay again.

Reviewed on May 18, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $3,410, price is now CA $2,288 per person
CA $2,288
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,721 reviews)
Parking was easy. The hotel breakfast and regular menu was really good! Elevators were at times a little inconvenient, but nothing too bad

Reviewed on May 19, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,379, price is now CA $1,605 per person
CA $1,605
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great!

Reviewed on May 19, 2026

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Homewood Hotel Deals

Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundable
The price is CA $152 per night from May 21 to May 22
CA $152
CA $178 total
May 21 - May 22
includes taxes & fees
8/10 Very Good! (1,869 reviews)
"Good"

Reviewed on May 20, 2026

Sleep Inn Midway Airport Bedford Park
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is CA $190 per night from May 24 to May 25
CA $190
CA $237 total
May 24 - May 25
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"it was ok"

Reviewed on May 19, 2026

Holiday Inn Chicago – Midway Airport S by IHG
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from May 27 to May 28
CA $168
CA $190 total
May 27 - May 28
includes taxes & fees
8.4/10 Very Good! (1,056 reviews)
"It was safe and people were friendly"

Reviewed on May 19, 2026

DoubleTree by Hilton Chicago - Alsip
See all 1,006 properties in Homewood
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 Homewood

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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 Homewood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Homewood

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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.