The Loop Vacations from $261

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Your The Loop Vacation

Experience the best that The Loop has to offer with a tailor-made The Loop vacation package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighborhood. 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 vacation into reality, no matter your budget or travel plans.

The Latest The Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
MainStay Suites Northbrook Wheeling

MainStay Suites Northbrook Wheeling

2.5 out of 5
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (882 reviews)
Great place for one person for leaving, better than apartment👍

Reviewed on Apr 4, 2025

Motel 6 Joliet, IL - I-80

Motel 6 Joliet, IL - I-80

2 out of 5
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (CHI)
5.4/10 (611 reviews)
Thank you for a cheap priced hotel room with wow factor design!

Reviewed on Apr 6, 2025

Holiday Inn Express Hotel & Suites, a Lake Zurich-Barrington by IHG

Holiday Inn Express Hotel & Suites, a Lake Zurich-Barrington by IHG

2.5 out of 5
per person
Jun 20 - Jun 22
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.8/10 Excellent! (776 reviews)
Parking in strip mall

Reviewed on Apr 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
It was really nice overall! Would recommend

Reviewed on Apr 28, 2025

Red Roof Inn Gurnee - Waukegan

Red Roof Inn Gurnee - Waukegan

2 out of 5
per person
Jun 19 - Jun 22
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
It’s was good and the place was super quiet

Reviewed on Apr 27, 2025

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 showing a city

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 $189 per night from May 27 to May 28
$189
includes taxes & fees
$161 per night
May 27 - May 28
7.8/10 Good! (8,729 reviews)
"Loved our stay! Cool historic hotel in an excellent location. Breakfast buffet was $29.95 and had wonderful variety of choices."

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $235 per night from May 1 to May 2
$235
includes taxes & fees
$200 per night
May 1 - May 2
8.8/10 Excellent! (2,072 reviews)
"The location was a little confusing at first, but once we became more familiar with the area, it was pretty conveniently located, right on the water and close to many busses. The staff was helpful and attentive."

Reviewed on Apr 29, 2025

Swissotel - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $164 per night from May 8 to May 9
$164
includes taxes & fees
$140 per night
May 8 - May 9
8.6/10 Excellent! (4,095 reviews)
"Thus property was beautiful, very clean, friendly staff and there was free coffee. Amazing views made it even better. We walked across the street to the River Walk and down the block to a boat tour. We also walked to a bar and a restaurant downtown. If we go back to Chicago, we would definitely stay ..."

Reviewed on Apr 27, 2025

River Hotel
See all 1,164 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

Kid Friendly Vacations

Kid Friendly Vacations

Discover the most popular places to visit in The Loop

Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

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

Millennium Park
Chicago Riverwalk which includes a city, a bay or harbor and a river or creek

Chicago Riverwalk

4.5/5(1,535 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 which includes art and interior views

Art Institute of Chicago

4.5/5(3,410 reviews)

Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.

Art Institute of Chicago

Things to do

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$45
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Color Factory Chicago Ticket

Color Factory Chicago Ticket

$34
per adult
100% of travellers recommend
Color Factory Chicago Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$22
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

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