Gresham Holidays from AU$525

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to AU$703 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 Gresham Holiday

Lock in your holiday package to Gresham and get ready to experience its cafes and beyond. Whether you're looking for fun or adventure, you'll discover it in this sought-after neighbourhood. No trip to Gresham is complete without checking out its top nearby attractions. Carter G. Woodson Library and Highland Community Bank are great places to start. Whatever your ideal Gresham holiday may look like, you can turn it into reality with Expedia.

Top Holiday Package Deals in Gresham

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
Downtown Chicago
Price was AU$745, price is now AU$525 per person
AU$525
per person
16 Nov - 19 Nov
found 1 day ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.6/10 Exceptional! (1,026 reviews)
It’s important for people who are planning on staying there that there is no bar and no restaurant inside the property. There was a restaurant attached to the hotel that served only breakfast and lunch. No dinner. This was somewhat disappointing.

Reviewed on 17 Oct 2025

The Drake

The Drake

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,011, price is now AU$603 per person
AU$603
per person
16 Nov - 19 Nov
found 1 day ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
8.8/10 Excellent! (1,291 reviews)
In spite of the great features, this overpriced hotel runs down with old furniture. We had a great beach front view but there is no direct access though.

Reviewed on 17 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,870, price is now AU$1,188 per person
AU$1,188
per person
16 Nov - 19 Nov
found 1 day ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on 15 Oct 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$914, price is now AU$634 per person
AU$634
per person
16 Nov - 19 Nov
found 1 day ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
excellent hotel, the staff, access to the city. We had a nice time in Chicago

Reviewed on 17 Oct 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,087, price is now AU$797 per person
AU$797
per person
16 Nov - 19 Nov
found 1 day ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Buen servicio limpieza y atención

Reviewed on 16 Oct 2025

Our guide on where to stay in Gresham

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

Our pick of the best Gresham 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
8/10 Very Good! (9,398 reviews)
"Was conveniently located"

Reviewed on 13 Oct 2025

Get rates
Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 10 Nov to 11 Nov
AU$147
10 Nov - 11 Nov
includes taxes & fees
7.8/10 Good! (2,475 reviews)
"Room needs to be cleaned a little thoroughly and then repainted but generally, I like the place"

Reviewed on 15 Oct 2025

Freehand Chicago
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 AU$203 per night from 16 Nov to 17 Nov
AU$203
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,088 reviews)
"Clean rooms, great service."

Reviewed on 13 Oct 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,508 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Gresham holiday package cost?
The most affordable Gresham package is AU$525, 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 holiday 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 holiday 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 holiday?
Travellers 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 holiday package is the most convenient way to organise 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 holiday 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 holiday package?
Don't stress if you're rethinking your Gresham holiday 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.

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.