The Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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.
  • 55-inch TV with cable channels, video-game console, pay movies
    Jul 1 - Jul 6

    Hilton Chicago O'Hare Airport + Flight

    O'Hare
    5 nights
    4.0 star property
    8.4/10 - Very good (2,310 reviews)
    "Good service but poor maintenance"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,473
    CA $1,021
    per traveller
    found 2 days ago
    Hilton Chicago O'Hare Airport
  • Full-size fridge, microwave, oven, stovetop
    Jul 23 - Jul 26

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (478 reviews)
    "Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby."
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,936
    CA $1,280
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Smart TV
    Aug 12 - Aug 16

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (481 reviews)
    "Yes"
    Reviewed May 12, 2026
    Roundtrip • Québec City (YQB) - Chicago (ORD)
    YQB - ORD • Nonstop ORD - YQB • Nonstop
    CA $2,106
    CA $1,485
    per traveller
    found 2 days ago
    Level Chicago Fulton Market
  • Premium bedding, pillowtop beds, in-room safe, individually furnished
    Jul 23 - Jul 26

    Level Chicago - River North + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,017 reviews)
    "Beautiful, clean, modern, and super convenient location. Away from the super busy, but only a few blocks walking to everything. It was perfect for our stay in Chicago!"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,889
    CA $1,332
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Indoor wedding
    Aug 12 - Aug 16

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,332 reviews)
    "Very good Outstanding service "
    Reviewed May 19, 2026
    Roundtrip • Québec City (YQB) - Chicago (ORD)
    YQB - ORD • Nonstop ORD - YQB • Nonstop
    CA $1,846
    CA $1,311
    per traveller
    found 2 days ago
    Swissotel - Chicago

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

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

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 CA $183 per night from May 26 to May 27
CA $183
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,162 reviews)
"A old, classic hotel and a low room rate, I was not expecting 'up to date modern'. Plusses: Room was large and clean, no noise from other guests, bag storage free, price compared to other hotels very low. Minuses: Unable to turn heater on _only a thin quilt blanket for bed, noise from toilet filling ..."

Reviewed on May 19, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $197 per night from May 25 to May 26
CA $197
CA $235 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,193 reviews)
"My stay at the River Hotel was excellent from start to finish. The location is unbeatable, making it easy to explore the surrounding area, and the views were a great bonus. The room was clean, comfortable, and well-maintained, with everything I needed for a relaxing stay."

Reviewed on May 18, 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 CA $241 per night from May 25 to May 26
CA $241
CA $336 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (2,163 reviews)
"Lovely stay and we are at Toro right in the hotel. Fabulous dinner"

Reviewed on May 18, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a The Loop vacation 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 vacation package makes it easy to organize 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 favorites with many travelers.
How far in advance should I book my The Loop vacation?
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 traveling 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 vacation 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 vacation package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop vacation 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

Millennium Park

4.5/5(736 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Chicago Riverwalk

Chicago Riverwalk

4.5/5(150 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
Willis Tower

Willis Tower

4.5/5(283 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Willis Tower

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago

Explore a world of travel with Expedia

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