Gresham Vacation Packages

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Your Gresham Vacation

Say goodbye to planning hassles and hello to a Gresham vacation package. With the finer details organized before you leave, you can focus on discovering this city, starting with Magnificent Mile, which is good for cafes, shopping and history. Need some sightseeing tips for your trip to Gresham? Carter G. Woodson Library and Highland Community Bank are two major attractions here. No matter your travel plans or the size of your budget, putting together a tailored Gresham vacation is a cinch with Expedia.

Top Holiday Package Deals in Gresham

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was CA $1,560, price is now CA $1,001 per person
CA $1,001
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
The property was clean and safe. The front desk was very nice.

Reviewed on Aug. 27, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,892, price is now CA $1,124 per person
CA $1,124
per person
Oct 3 - Oct 8
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug. 25, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $2,075, price is now CA $1,322 per person
CA $1,322
per person
Nov 3 - Nov 6
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,768, price is now CA $1,128 per person
CA $1,128
per person
Oct 13 - Oct 17
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (339 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,562, price is now CA $1,642 per person
CA $1,642
per person
Oct 13 - Oct 17
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

Where to stay in Gresham

Find the best Gresham areas and neighborhoods for the activities you enjoy most. Learn more about Gresham
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Gresham Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $447 per night from Sep 26 to Sep 27
CA $447
CA $525 total
Sep 26 - Sep 27
includes taxes & fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on Aug. 24, 2025

The Wade
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 $186 per night from Sep 1 to Sep 2
CA $186
CA $218 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,992 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on Aug. 23, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is CA $211 per night from Sep 3 to Sep 4
CA $211
CA $247 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,752 reviews)
"Great location. Nice size rooms. Breakfast was really good, only way to busy and crowded during that experience. They should extend the breakfast hours by an hour to reduce the over crowding. Overall good stay. Would return.."

Reviewed on Aug. 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,628 properties in Gresham
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.
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Frequently asked questions

How much does a Gresham vacation package cost?
The most affordable Gresham package is CA $1,001, so the trip of your dreams can become a reality — without breaking the bank. Bundle flights, hotels, car rentals and more to create a package that matches your travel style.
How do I get a cheap travel package to Gresham?
Our Gresham vacation packages mean plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and activities into one neat package. But bargain prices are only the start of your next big adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotel options all over the world to choose from. Whatever your style or budget, there's a vacation package with your name on it.
Where should I stay in Gresham?
With so much to do in Gresham, it's a good idea to secure a room in a hotel close to its attractions. Dr. Percy Julian Residence, Highland Community Bank and Carter G. Woodson Library are some fascinating ones to put on your to-do list.
How far in advance should I book my Gresham vacation?
Travelers can normally browse international airfares on Expedia within 12 months of departure. Booking late? With a bit of luck, it's still possible to purchase a cheap ticket just weeks before your flight.
What does an Expedia Gresham travel package include?
Packages include hotels, flights and rental cars, but you can combine any of them to create your ideal Gresham getaway. You can also add on fun stuff like activities and experiences once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.
What should I know before booking a Gresham travel package?
Bundling your bookings into a Gresham vacation package is the most convenient way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Gresham Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply select your preferred carrier and craft your ideal Gresham escape.
If I'm not able to travel, can I cancel my Gresham vacation package?
Don't stress if you're rethinking your Gresham vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally get that your circumstances can change suddenly, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Things to do

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
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 Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.