Greater Grand Crossing Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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.
  • Indoor wedding
    Jul 6 - Jul 12

    Swissotel - Chicago + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.0/10 - Wonderful (3,365 reviews)
    "Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
    Reviewed June 6, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,440
    £1,095
    per traveller
    found 21 hours ago
    Swissotel - Chicago
  • Lobby sitting area
    Jul 6 - Jul 12

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    8.4/10 - Very good (1,959 reviews)
    "Ñ"
    Reviewed June 6, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,514
    £1,124
    per traveller
    found 21 hours ago
    Hotel Saint Clair- Magnificent Mile
  • Terrace/patio
    Jul 11 - Jul 18

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,526 reviews)
    "Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission."
    Reviewed June 4, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    £1,965
    £1,469
    per traveller
    found 17 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 12 - Aug 16

    Level Chicago – Old Town + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.0/10 - Wonderful (488 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Return • Manchester (MAN) - Chicago (ORD)
    MAN - ORD • 1 stop ORD - MAN • 1 stop
    £1,904
    £1,430
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Terrace/patio
    Jul 11 - Jul 18

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,882 reviews)
    "We love the pool, cleanliness in the room .Friendly staff"
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    Save 100% on your flight
    £2,676
    £2,033
    per traveller
    found 17 hours ago
    Trump International Hotel & Tower Chicago

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 £124 per night from 29 Jun to 30 Jun
£124
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,178 reviews)
"Location was good to train station and grand park but biggest issue we had is no water pressure and it was at best lukewarm. This makes me now want to always check first before booking anything how their water service is. It was terrible and when I checked previous reviews it was one of biggest complaints. ..."

Reviewed on 6 Jun 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 £135 per night from 28 Jun to 29 Jun
£135
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,522 reviews)
"Had a great stay and the staff were excellent and very accommodating. Location is perfect for anyone looking to stay close to the Magnificent Mile. You can park your car and walk to everything. Highly recommend!"

Reviewed on 6 Jun 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 £190 per night from 30 Jun to 1 Jul
£190
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,358 reviews)
"Excelente atención de todo el personal del hotel. Muy limpio todo, un desayuno super bueno y muy variado. El rooftop con excelente servicio y ofertas, además de vistas increíbles. Excelente ubicación. Definitivamente la cadena hotelera Riu se ha convertido en mi favorita para cualquier destino🤗"

Reviewed on 5 Jun 2026

Hotel Riu Plaza Chicago
See all 4,564 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
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 . 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
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
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.