The Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

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

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

Find hotels in Downtown Chicago

Top hotels in The Loop

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 3.519.573 ₫ per night from 26 May to 27 May
3.519.573 ₫
4.184.418 ₫ total
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,150 reviews)
"Always stay here when I’m trying to save money great location and price"

Reviewed on 17 May 2026

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 4.009.457 ₫ per night from 25 May to 26 May
4.009.457 ₫
4.766.844 ₫ total
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,188 reviews)
"The property was in excellent condition and excellent location on the riverfront and easy walk to Michigan Ave shops and restaurants. The only downside is that this whole area is extremely loud well past 3am(loud motorcyclists, cars revving and loud music from passing cars). It was impossible to ..."

Reviewed on 18 May 2026

River Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is 5.312.563 ₫ per night from 25 May to 26 May
5.312.563 ₫
7.256.083 ₫ total
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (2,161 reviews)
"Lovely stay and we are at Toro right in the hotel. Fabulous dinner"

Reviewed on 18 May 2026

Fairmont Chicago at Millennium Park
See all 1,233 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.

Frequently asked questions

How much does a The Loop holiday package cost?
Much less than you might think — from as low as , 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 1null000null000 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.

Popular places to visit

Millennium Park

Millennium Park

4.5/5(147 reviews)

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Millennium Park
Willis Tower

Willis Tower

4.5/5(81 reviews)

Willis Tower is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed theatre scene in this vibrant area.

Willis Tower
Art Institute of Chicago

Art Institute of Chicago

4.5/5(66 reviews)

You can spend an afternoon browsing the exhibits at Art Institute of Chicago in Chicago. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.

Art Institute of Chicago