The Loop Holidays from AU$2,121
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your The Loop Holiday
Experience the best that The Loop has to offer with a tailor-made The Loop holiday package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighbourhood. Your trip to The Loop wouldn't be complete without seeing popular attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal The Loop holiday into reality, no matter your budget or travel plans.
The Latest The Loop Holiday Packages
- Hotel Felix River North/Magnificent Mile
25 Jan - 28 JanHotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.4/10 - Very good (3,176 reviews)"Overall, great location and the bed was extremely comfortable, but keep in mind that the rooms don't have a mini fridge or coffee maker, and if you need shower caps, bring one from home! It's a boutique hotel in downtown Chicago, so it doesn't offer as much in the actual room as other hotels in other cities I've stayed in. Overall, I would recommend it. If you have a car to park, it's valet service only and it's $74 USD per day."Reviewed November 10, 2026Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$3,293AU$2,121found 1 day agoper traveller - Park Hyatt Chicago
25 Jan - 28 JanPark Hyatt Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,003 reviews)Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$4,430AU$2,847found 1 day agoper traveller - The Talbott, Autograph Collection
25 Jan - 28 JanThe Talbott, Autograph Collection + Flight
Downtown Chicago3 nights4.5 star property9.4/10 - Exceptional (197 reviews)Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$3,635AU$2,346found 1 day agoper traveller - Trump International Hotel & Tower Chicago
25 Jan - 28 JanTrump International Hotel & Tower Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (2,082 reviews)"Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨"Reviewed November 9, 2026Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$4,057AU$2,628found 1 day agoper traveller - Kinzie Hotel
25 Jan - 28 JanKinzie Hotel + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (2,183 reviews)Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$3,375AU$2,202found 1 day agoper traveller
Our guide on where to stay in The Loop
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
West Loop
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Discover the most popular places to visit in The Loop
What to do near The Loop
Skydeck Chicago at Willis Tower
The Loop Hotel Deals
"Incredible hotel n gorgeous lake view. Staff were so friendly and helpful. Loved it. Will stay here again for sure!"
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton"Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile....
Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre District"Breakfast was good. Morning staff was helpful. Bathroom was clean. My only recommendation is that the chairs in the room get replaced soon. Overall, a good experience at a reasonable price."
Cambria Hotel Chicago Loop - Theatre District
Cambria Hotel Chicago Loop - Theatre District"Clean room"
"Rooms were modern looking, functional and beds were so comfy"
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown"1500 characters are not enough to describe the roach motel feel and the attitude given for wanting to not be disgusted by the room you were assigned. Wasn't expecting fancy, but did expect clean and functional.. 2 expectations that apparently were set too high. Walking on the bathroom floor sounded like velcro being pulled apart from your shoes sticking to the tile. The shower drain looked like a chia pet with human hair. The carpet was disgusting, and their solution apparently was to...
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Every thing is good!👍🌹"
Frequently Asked Questions
How much does a The Loop holiday package cost?
Much less than you might think — from as low as AU$2,121, in fact! By bundling flights, hotels and car rentals into your own custom-made package, your The Loop escape is only clicks away.
How do I get a cheap travel package to The Loop?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you cash too. A The Loop holiday package makes it easy to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1 000 000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia will help show you the world.
Where should I stay in The Loop?
A journey to The Loop isn't over until you've seen McCormick Place and Millennium Park. Look for somewhere to stay within walking distance so you can easily access these impressive tourist attractions.
What are the top hotels in The Loop?
If it's your first time staying in The Loop, make a reservation at Canopy by Hilton Chicago Central Loop or Hilton Garden Inn Chicago Central Loop. Both hotels offer comfy beds and are favourites with many travellers.
How far in advance should I book my The Loop holiday?
To bag rock-bottom prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to The Loop, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia The Loop travel package include?
That depends on what you want. If you're travelling solo, you might decide to bundle flights and hotels. Taking the whole family to The Loop? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
Can I choose my airline with a The Loop Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to choose from globally. With so many choices, finding the ideal carrier to whisk you away to The Loop will be a snap.
If I'm not able to travel, can I cancel my The Loop holiday package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop holiday package and need to cancel or change it, we're here to help. We recommend browsing our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel and rebook for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.