Greater Grand Crossing Holidays from £556

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Your Greater Grand Crossing Holiday

Our Greater Grand Crossing holiday packages are a speedy and practical way to plan and book your next exciting adventure. Uncover the magic of this unique neighbourhood without the fuss of organising it all yourself. Hoping to explore the sights during your trip to Greater Grand Crossing? Be sure to check out nearby attractions 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 ultimate Greater Grand Crossing holiday now.

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,001, price is now £556 per person
£556
per person
27 May - 30 May
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,120 reviews)
I have stayed at a few Fairmount properties in the past and I would say this was not my favorite of the brand. Overall a nice hotel but not for the price point.

Reviewed on 20 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,619, price is now £1,130 per person
£1,130
per person
10 Jun - 15 Jun
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!

Reviewed on 20 Apr 2026

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £761, price is now £556 per person
£556
per person
27 May - 30 May
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (1,520 reviews)
Have stayed on many occasions at the Claridge as it is a smaller hotel and located just where I like to be on the Gold Coast. Staff super friendly and helpful, have a nice happy hour. Only issue I had this trip is that our room was a terrible design, particularly that of the bathroom which seems to be stuck in where they could fit it. Difficult to navigate during the night, tight quarter and awkward door position. Other than that , had a great stay but would not stay again in that room

Reviewed on 21 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,717, price is now £1,266 per person
£1,266
per person
10 Jun - 15 Jun
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
10/10 highly recommend

Reviewed on 21 Apr 2026

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,130, price is now £834 per person
£834
per person
27 May - 30 May
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
Fantastic from desk staff *Robert. Clean, upgraded room. The "rooftop" restaurant was fantastic as well. Close proximity to all of the wonderful shopping!

Reviewed on 20 Apr 2026

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

Top hotels in Greater Grand Crossing

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 £100 per night from 26 Apr to 27 Apr
£100
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,160 reviews)
Hotel has the markings of being grand, but needs a renovation in a lot of areas. The biggest issue we had is that the a/c is not adjustable in each room and the building was very warm on the 75 degree day in April. We called the front desk and they did bring us a fan that helped some and we realized ...

Reviewed on 20 Apr 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is £129 per night from 22 Apr to 23 Apr
£129
22 Apr - 23 Apr
includes taxes & fees
8.8/10 Excellent! (5,114 reviews)
Really good location

Reviewed on 20 Apr 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £98 per night from 26 Apr to 27 Apr
£98
26 Apr - 27 Apr
includes taxes & fees
8.2/10 Very Good! (2,636 reviews)
The room was actually pretty good and pretty good size for two people and a queen bed I really loved it and I would go back again.

Reviewed on 21 Apr 2026

Hotel Felix River North/Magnificent Mile
See all 4,648 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
All Inclusive Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Greater Grand Crossing travel package cost?
Custom make your Greater Grand Crossing package from as little as £556. Choose from any combination of hotels, flights and rental cars to put together the escape you've been dreaming about. Be sure to add on some tours and experiences!
If I'm not able to travel, can I cancel my Greater Grand Crossing travel package?
Yes, you can cancel your Greater Grand Crossing booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Greater Grand Crossing?
Browse and lock in everything all in one place with our Greater Grand Crossing travel packages. You'll discover deals on flights, hotels and more that'll keep your pocket happy and your adventurous side busy. And, with more than 550 airlines and 1,000,000 hotel options around the world to choose from, you'll have the flexibility to mix and match as you please.
Does Expedia offer Book Now, Pay Later Greater Grand Crossing holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply pick the payment plan best suited to your needs during checkout and take away the stress of budgeting for your next trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: If you'd prefer to pay off your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this option. Just put down a small deposit on your escape and then start working on your travel plans.

Where should I stay in Greater Grand Crossing?
A trip to Greater Grand Crossing isn't complete without stopping by Millennium Park and Wrigley Field. Book a room within walking distance so you can easily access these popular attractions.
What are the top hotels in Greater Grand Crossing?
Make a reservation at Hyatt Regency Chicago. It's one of the neighbourhood's most sought-after hotels. Another well-known option in Greater Grand Crossing is The Godfrey Hotel Chicago.
How far in advance should I book my Greater Grand Crossing holiday?
It can be tricky to know when is the ideal time to book your Greater Grand Crossing trip. But usually the earlier you book, the better the prices. In some cases, you can lock in your flights and hotels nearly 12 months before your departure date. If you're thinking of a last-minute getaway, no need to panic! There are fabulous deals popping up on Expedia all the time.
What does an Expedia Greater Grand Crossing travel package include?
Choose from a combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like activities and experiences. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to putting together your perfect Greater Grand Crossing getaway.
What should I know before booking a Greater Grand Crossing travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, you can add on sightseeing tours or experiences. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Greater Grand Crossing Expedia travel package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 airline partners across the globe, so you have lots of choice when organising your Greater Grand Crossing escape.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in 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. Flight-inclusive packages are ATOL protected.