South Loop Holidays

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Where to stay in South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South 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

Top hotels in South 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 Rp1.989.273 per night from 26 Apr to 27 Apr
Rp1.989.273
Rp2.335.511 total
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,133 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...

Reviewed on 24 Apr 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is Rp2.739.411 per night from 25 May to 26 May
Rp2.739.411
Rp3.762.986 total
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (2,748 reviews)
It was a very pleasant stay. The staff was superb loved the hotel, its history, and experience.

Reviewed on 23 Apr 2026

Hilton Chicago
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
The price is Rp2.324.621 per night from 10 May to 11 May
Rp2.324.621
Rp2.763.905 total
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (1,956 reviews)
Nice clean hotel. Breakfast nearby

Reviewed on 23 Apr 2026

Hilton Garden Inn Chicago Downtown South Loop
See all 4,725 properties in South 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 South Loop holiday package cost?
Starting from a low , a holiday package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to South Loop?
Creating your own South Loop holiday package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you'll have no trouble creating your next dream getaway.
Where should I stay in South Loop?
Make sightseeing a breeze by staying someplace close to South Loop's iconic attractions. McCormick Place and Millennium Park are two of the best in the area.
What are the top hotels in South Loop?
Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?
How far in advance should I book my South Loop holiday?
It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you're hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.
What does an Expedia South Loop travel package include?
That depends on what type of getaway you're thinking about. South Loop holiday deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a South Loop travel package?
So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a South Loop Expedia holiday package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that's a good fit for your needs.
If I'm not able to travel, can I cancel my South Loop holiday package?
Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Popular places to visit

Northerly Island Natural Area

Northerly Island Natural Area

Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.

Northerly Island Natural Area

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp459.054
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

Rp703.203
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.853.218
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.