The Loop Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*
  • Find the right fit

    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.
  • Aug 14 - Aug 16

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Great day super nice staff and very helpful comfortable clean, and a great location at a reasonable price very pleased"
    Reviewed May 20, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$999
    NZ$787
    per traveller
    found 7 hours ago
    Le Méridien Essex Chicago
  • Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,715 reviews)
    "A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."
    Reviewed May 22, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,164
    NZ$878
    per traveller
    found 7 hours ago
    Hotel Felix River North/Magnificent Mile
  • Aug 14 - Aug 16

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    8.8/10 - Excellent (2,164 reviews)
    "Amazing staff. Clean rooms!"
    Reviewed May 21, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,127
    NZ$859
    per traveller
    found 7 hours ago
    Fairmont Chicago at Millennium Park
  • Aug 14 - Aug 16

    L7 Chicago by LOTTE + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.6/10 - Exceptional (4,076 reviews)
    "The property has a very convenient location. The room is spacious. They offer free but good coffee and popcorn at the lobby every day. And the cold water from the tab is filtered. Definitely will come back."
    Reviewed May 22, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,106
    NZ$885
    per traveller
    found 7 hours ago
    L7 Chicago by LOTTE
  • Aug 14 - Aug 16

    Swissotel - Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.0/10 - Wonderful (3,336 reviews)
    "Great location and very convenient to river walk and vicinity."
    Reviewed May 22, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,201
    NZ$964
    per traveller
    found 7 hours ago
    Swissotel - Chicago

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

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 NZ$271 per night from 25 May to 26 May
NZ$271
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,131 reviews)
"Did not have hot water when we returned to room after concert. Next morning called and maintenance came to fix. Good location to walk to South Shore train station and Grant Park"

Reviewed on 23 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 NZ$240 per night from 26 May to 27 May
NZ$240
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,190 reviews)
"The staff was very helpful and friendly."

Reviewed on 22 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 NZ$401 per night from 25 May to 26 May
NZ$401
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (2,164 reviews)
"Amazing staff. Clean rooms!"

Reviewed on 21 May 2026

Fairmont Chicago at Millennium Park
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 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

Activities

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.