The Loop Holidays from AU$620

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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.

Top Holiday Package Deals in The Loop

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
San Francisco (SFO) to Chicago (ORD)
8.8/10 Excellent! (1,923 reviews)
Views were unbelievable! No streaming services were available, and the breakfast server in part was abrupt, but overall, it was a great stay.

Reviewed on 21 Dec. 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 22 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (275 reviews)
I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location

Reviewed on 7 Dec. 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 19 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,246 reviews)
Great location to a lot of things to do in Chicago

Reviewed on 22 Dec. 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 19 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (931 reviews)
Excellent service at front desk, coffee shop and Fora. Very clean and fun atmosphere. Beds extremely comfortable! Friendly employees. Easy to walk to sops and restaurants. Highly recommend

Reviewed on 18 Dec. 2024

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 19 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
7.8/10 Good! (8,267 reviews)
Wallpaper in lobby is old. No working ice machines to be found.

Reviewed on 21 Dec. 2024

Our guide on where to stay in The Loop

Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop
Downtown Chicago featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Our pick of the best The Loop 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 AU$196 per night from 23 Dec to 24 Dec
AU$196
includes taxes & fees
23 Dec - 24 Dec
7.8/10 Good! (8,270 reviews)
"Wallpaper in lobby is old. No working ice machines to be found."

Reviewed on 21 Dec. 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 21 Jan to 22 Jan
AU$175
includes taxes & fees
21 Jan - 22 Jan 2025
8.6/10 Excellent! (3,620 reviews)
"This hotel is great! The staff helped us check in early and provided us with a river view room. My friend and I were both very happy^^ Although it’s close to the busy road, the room is not noisy. The location of the hotel is also very good, making our travel convenient."

Reviewed on 17 Dec. 2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$324 per night from 5 Jan to 6 Jan
AU$324
includes taxes & fees
5 Jan - 6 Jan 2025
9/10 Wonderful! (3,114 reviews)
"I loved my stay. One of the best hotels in the city."

Reviewed on 18 Dec. 2024

Hyatt Regency Chicago
See all 1,271 properties in The Loop
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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a The Loop holiday package cost?
Much less than you might think — from as low as AU$620, 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.

Discover the most popular places to visit in The Loop

Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Willis Tower showing interior views, views and city views

Willis Tower

4.5/5(39 reviews)

The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.

Willis Tower
Art Institute of Chicago showing art and interior views

Art Institute of Chicago

4.5/5(32 reviews)

From ancient masterpieces to eclectic modern art, uncover a treasure trove of works from all over the world and throughout history.

Art Institute of Chicago

Activities

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$69
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Color Factory Chicago Ticket

Color Factory Chicago Ticket

AU$52
per adult
Color Factory Chicago Ticket
Private Chicago Scavenger Hunt: Eastside Art Heist

Eastside Chicago The Heist Exploration Game and Tour

AU$16
per adult
Eastside Chicago The Heist Exploration Game and Tour
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.