Galewood Holidays

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  • Better together

    Save up to €900 when you book a flight and hotel together*

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    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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €618, price is now €391 per person
€391
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Clean, cozy, and updated. The shampoo and conditioner was amazing!! Consider selling it to guests!

Reviewed on 12 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,541, price is now €895 per person
€895
per person
25 Sept - 30 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,407, price is now €842 per person
€842
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,408, price is now €874 per person
€874
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Staff was very friendly and helpful, room had an amazing harbor view, and everything was clean and well tidy. Great location on the pier and we were able to walk downtown which was about a mile away.

Reviewed on 12 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was €787, price is now €499 per person
€499
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Loved the size of our room and how clean it was.

Reviewed on 9 Jul 2026

Where to stay in Galewood

Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood
A busy city street with tall buildings, a bus, and cars.

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 Galewood

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 27 Jul to 28 Jul
€160
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,736 reviews)
"Good location, nice lobby, sparse rooms."

Reviewed on 12 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
The price is €270 per night from 26 Jul to 27 Jul
€270
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,912 reviews)
"Of course thr location is great for shopping and restaurants, and walks to the park, but are room was great with plenty of room. The staff at the hotel was fantastic."

Reviewed on 12 Jul 2026

Omni Chicago Hotel
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 €197 per night from 10 Aug to 11 Aug
€197
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,236 reviews)
"Neighboring room was extremely loud for two days straight. Someone rattled our doorknob around 3 am and started saying hello. Not acceptable by my standards. The bar was goofy they make drinks inappropriately and were out of stock of many basic things. Not planning on returning again"

Reviewed on 12 Jul 2026

Congress Plaza Hotel
See all 4,723 properties in Galewood
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 holiday package cost?
From just €391. Yes, you read that right. Our Galewood packages are a simple way to make your dollars go much further. Combine your favourite 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 holiday 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 holiday 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 holiday fantasies.
Where should I stay in Galewood?
Most who travel to Galewood include University of Illinois Chicago and United Centre 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 holiday?
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 holiday 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. Holidaying 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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday package?
Plans can change in the blink of an eye, so yes, you can. You may be able to cancel or alter your Galewood holiday 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€35
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.