Deals on vacations and trips to The Loop

Choose two or more items and save on your trip:

The Loop flight + hotel vacation packages

JW Marriott Chicago
Fairmont Chicago at Millennium Park Gold Experience
Park Hyatt Chicago
Trump International Hotel & Tower Chicago
Level Chicago – Old Town
Prices and availability subject to change. Additional terms may apply.

Top The Loop hotels deals

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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.

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Frequently asked questions

How much are vacation packages to The Loop?
Spoil yourself with a memorable travel experience in The Loop with a vacation package starting from just $644. Organizing your hotels, flights and tours through Travelocity is easy. And even better, our vacation deals will leave you with more savings in your pocket for fun activities.
Where can I get the best vacation package deals for The Loop?
Picking up an amazing package deal to The Loop is a breeze with Travelocity. With around 400 partner airlines and 1,000,000 properties around the world, you won’t be short of choice when picking your flights and hotels.
Why should I purchase my The Loop vacation package via Travelocity?
From our 24/7 customer support to our range of fantastic destinations, we are committed to fulfilling your travel desires. All you have to do is to click and book — our Price Match Guarantee will ensure you score the best deal.
Can I save on my The Loop car rental if I combine it with a hotel or flight?
You certainly can — and booking one of our The Loop vacation packages is the best way to do this. Bundle any combination of a car, flight, hotel and experience and score awesome discounts. The more you book, the more you save. There are plenty of big-name sights in and around The Loop that are worth a road trip, including Six Flags Great America (35 mi from The Loop). Nothing tops exploring places like this with the freedom of your own car rental.
What is the best time of year to go to The Loop?
You’ll score the lowest hotel prices in and pay the highest prices in . You can expect it to be less busy in January, September and December, while you’ll have more like-minded travelers to meet during the months of March, May and June. It all comes down to what prices you’re willing to pay, the weather and how well you deal with crowds.