Greater Grand Crossing Holidays

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Your Greater Grand Crossing Holiday

Organising your next break just got easier with a holiday package to Greater Grand Crossing. Embrace the best this neighbourhood has to offer while making fond memories you won't forget. Your trip to Greater Grand Crossing wouldn't be complete without exploring major attractions nearby such as University of Chicago, Chicago Museum of Science and Industry and Robie House. Expedia is here to help put your travel plans into action. Book your ideal Greater Grand Crossing holiday today.

Price found within the past 48 hours. Click for updated prices.
  • Breakfast and dinner served
    Aug 14 - Aug 16

    Omni Chicago Hotel + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (1,789 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$991
    AU$739
    per traveller
    found 1 day ago
    Omni Chicago Hotel
  • Serves breakfast, lunch and dinner
    Aug 14 - Aug 16

    JW Marriott Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it."
    Reviewed May 31, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,110
    AU$806
    per traveller
    found 1 day ago
    JW Marriott Chicago
  • Premium bedding, pillow-top beds, in-room safe, individually furnished
    Aug 14 - Aug 16

    Level Chicago - River North + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,012 reviews)
    "I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,094
    AU$825
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Terrace/patio
    Aug 14 - Aug 16

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    2 nights
    5.0 star property
    9.6/10 - Exceptional (1,879 reviews)
    "Great stay and location."
    Reviewed June 4, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    AU$1,591
    AU$1,200
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Lobby
    Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,750 reviews)
    "Hotel staff was super nice. Great location to be in walking distance of a lot of places."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,034
    AU$781
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile

Our guide on where to stay in Greater Grand Crossing

Find the best Greater Grand Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Greater Grand Crossing
Downtown Chicago

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 Greater Grand Crossing 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 AU$231 per night from 29 June to 30 June
AU$231
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,166 reviews)
"Apparently it's haunted and I had the room across the hall from the haunted room. I didn't know this until my third night there, but it was quiet and calm."

Reviewed on 4 June 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is AU$253 per night from 28 June to 29 June
AU$253
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,512 reviews)
"Clean room"

Reviewed on 3 June 2026

The Chicago Hotel Collection - Magnificent Mile
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 AU$355 per night from 30 June to 1 July
AU$355
30 June - 1 July
includes taxes & fees
9.4/10 Exceptional! (4,331 reviews)
"Urine in toilet upon entering, garbage left in room , rooftop glass floor closed not mentioned"

Reviewed on 4 June 2026

Hotel Riu Plaza Chicago
See all 4,575 properties in Greater Grand Crossing
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
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Frequently asked questions

How much does a Greater Grand Crossing holiday package cost?
Live it up in Greater Grand Crossing from just . Choose from a wonderful selection of hotels, flights and rental cars to suit every budget and style. Pick up even better deals when you add some activities or tours to your package.
How do I get a cheap travel package to Greater Grand Crossing?
Just imagine all the fabulous things you could do in Greater Grand Crossing with extra cash in your wallet. Watch your savings stack up when you bundle your travel bookings into a Greater Grand Crossing holiday package. You have plenty of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1 000 000 properties around the world. Whether you're taking off with the entire family or going it alone, organising a getaway to Greater Grand Crossing is better with a package.
Where should I stay in Greater Grand Crossing?
A visit to Greater Grand Crossing isn't complete without seeing University of Chicago and Chicago Museum of Science and Industry. Reserve a room close by for quick access to these famous sights.
How far in advance should I book my Greater Grand Crossing holiday?
While not all airlines advertise ticket prices early, customers are usually able to look up international flights on Expedia up to 12 months in advance. This is the time when you can nab some incredible bargains. If you're purchasing tickets last minute, you might still be in luck. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Greater Grand Crossing travel package include?
That depends on you. You can select from a variety of Greater Grand Crossing packages, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal Greater Grand Crossing break looks like, get set to save!
What should I know before booking a Greater Grand Crossing travel package?
You'll pick up great savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything in one place just makes things easier. So why waste your time or money? Whether you're organising a luxury city stay with your love or a budget solo adventure, take a look at our holiday packages today.
Can I choose my airline with a Greater Grand Crossing Expedia holiday package?
Yes, and with more than 550 airlines to choose from worldwide, you have loads of choice. Take a look at the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Greater Grand Crossing holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Greater Grand Crossing holiday package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Greater Grand Crossing

Greater Salem Baptist Church

After visiting Greater Salem Baptist Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Greater Salem Baptist Church

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$63
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
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.