Galewood Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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
Price found within the past 48 hours. Click for updated prices.
  • Jul 1 - Jul 6

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very Good (2,742 reviews)
    Roundtrip Tokyo (NRT) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥351,570
    ¥300,654
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Jul 1 - Jul 6

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (4,311 reviews)
    "I loved everything about this hotel. Great staff, great location and amazing rooftop."
    Reviewed June 1, 2026
    Roundtrip Tokyo (NRT) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥413,302
    ¥326,616
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Jul 1 - Jul 6

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,363 reviews)
    "The gym is on 43 floor.. amazing"
    Reviewed May 31, 2026
    Roundtrip Tokyo (NRT) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥377,793
    ¥307,578
    per traveler
    found 1 day ago
    Swissotel - Chicago
  • Jul 1 - Jul 6

    The Langham, Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    "Ask for a water view!"
    Reviewed May 31, 2026
    Roundtrip Tokyo (NRT) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥491,549
    ¥413,830
    per traveler
    found 1 day ago
    The Langham, Chicago
  • Jul 1 - Jul 6

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    "Great hotel. Loved the lobby and our room. Would definitely stay here again."
    Reviewed May 19, 2026
    Roundtrip Tokyo (NRT) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥397,201
    ¥340,096
    per traveler
    found 1 day ago
    Kimpton Gray Hotel by IHG

Where to stay in Galewood

Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood

Galewood 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 ¥22,218 per night from Jun 29 to Jun 30
¥22,218
¥26,415 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,142 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on May 31, 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 ¥24,209 per night from Jun 28 to Jun 29
¥24,209
¥28,783 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,498 reviews)
"Everything was great"

Reviewed on May 31, 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 ¥30,104 per night from Jun 30 to Jul 1
¥30,104
¥40,329 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,311 reviews)
"Fantastic stay. The location is perfect. The breakfast was superb and the roodtop bar fantastic"

Reviewed on Jun 1, 2026

Hotel Riu Plaza Chicago
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.

Frequently asked questions

How much does a Galewood vacation package cost?
From just . Yes, you read that right. Our Galewood packages are a simple way to make your dollars go much further. Combine your favorite hotels, flights and rental car and get out and explore this wonderful destination.
How do I get a cheap travel package to Galewood?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a Galewood vacation package to save loads of cash. Score even better deals when you add extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to put together your vacation your own way. We offer more than 550 airlines and 1,000,000 properties throughout the world, so that everyone has an opportunity to travel and live out those vacation fantasies.
Where should I stay in Galewood?
Most who travel to Galewood include University of Illinois Chicago and United Center on their sightseeing itineraries. Why not reserve a hotel as close as possible to these main attractions?
How far in advance should I book my Galewood vacation?
It's always wise to book early. Air carriers usually advertise flight tickets around a year ahead of departure, and this is when you can land some rock-bottom prices. Just been told you should take some vacation time next week? That's alright! Expedia are never short of fantastic deals to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Galewood travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Galewood package that's ideal for you. Vacationing for a week or longer? Consider a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, an airfare and hotel deal may be more your style. Activities can also be added after you've booked. Our travel packages make it a breeze to save and plan.
What should I know before booking a Galewood travel package?
Our prices are already low. However, you'll snap up even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and tons of choice.
Can I choose my airline with a Galewood Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to choose. We have more than 550 airline partners across the globe, so you have loads of choice when putting together your Galewood adventure.
If I'm not able to travel, can I cancel my Galewood vacation package?
Plans can change in the blink of an eye, so yes, you can. You may be able to cancel or alter your Galewood vacation package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may impose a fee. Looking for more information? Check out our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Galewood

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.