The Loop Holidays from AU$2,747

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 10 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8/10 Very Good! (1,433 reviews)
I liked that the hotel was very close to all of the places we were going to, however I found the the hotel was in a tough spot when it came to finding parking. I did manage to find public parking just fine the side walk after driving around for 20 min.

Reviewed on 15 Feb. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
4 May - 10 May
found 10 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,550 reviews)
Wonderful check-in experience, slow weekend in Chicago I guess because I was given a wonderful upgrade. My room is as big as an apartment

Reviewed on 12 Feb. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 10 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (287 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on 20 Jan. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 10 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (998 reviews)
A very nice hotel. Good location with many restaurants in the area.

Reviewed on 14 Feb. 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
4 May - 10 May
found 10 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
I was upset that the elevators were not working and it took a long to get to my room and the lobby. I would have appreciated communication about this ahead of time and would have switched hotels. Apparently it had been an issue for at least two weeks. The staff were amazing. The rooms were dark and small.

Reviewed on 14 Feb. 2025

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 Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels 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$158 per night from 17 Feb to 18 Feb
AU$158
includes taxes & fees
17 Feb - 18 Feb
7.8/10 Good! (8,473 reviews)
"The last day of my stay, a guy with a huge balloon in the shape of a rat was making a lot of noise with a speaker at the main door of the hotel, something very unpleasant. I don't understand why the hotel allowed that."

Reviewed on 12 Feb. 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 17 Feb to 18 Feb
AU$222
includes taxes & fees
17 Feb - 18 Feb
9.6/10 Exceptional! (1,627 reviews)
"all good"

Reviewed on 14 Feb. 2025

L7 Chicago by LOTTE
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$321 per night from 22 Feb to 23 Feb
AU$321
includes taxes & fees
22 Feb - 23 Feb
8.2/10 Very Good! (1,643 reviews)
"I look forward to staying again!"

Reviewed on 3 Feb. 2025

Hilton Chicago
See all 1,299 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$2,747, 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
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

4.5/5(26 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk
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

Color Factory Chicago Ticket

Color Factory Chicago Ticket

AU$55
per adult
100% of travellers recommend
Color Factory Chicago Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$72
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Private Chicago Scavenger Hunt: Eastside Art Heist

Eastside Chicago The Heist Exploration Game and Tour

AU$20
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.