South Loop Vacations from ￥105,900

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The Latest South Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥133,123, price is now ￥105,900 per person
￥105,900
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The bar was fine we got 2 free drinks.

Reviewed on Apr 1, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥181,360, price is now ￥120,048 per person
￥120,048
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer. Buffet breakfast is included and that makes it very good value. Hotel also has a gym/ Not too many amenities in the room though.

Reviewed on Apr 2, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥207,780, price is now ￥156,566 per person
￥156,566
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.

Reviewed on Mar 31, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥148,203, price is now ￥117,789 per person
￥117,789
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel was better than I expected due to some reviews I had saw online! I really enjoyed my stay here!

Reviewed on Apr 2, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥156,968, price is now ￥126,060 per person
￥126,060
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
Nice staff, clean rooms, however elevator is slow

Reviewed on Apr 2, 2026

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

South 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 ￥17,185 per night from Apr 5 to Apr 6
￥17,185
￥20,173 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,007 reviews)
Good location for where we needed to be in the city. It’s a very dated hotel.

Reviewed on Apr 2, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥33,342 per night from Apr 10 to Apr 11
￥33,342
￥43,821 total
Apr 10 - Apr 11
includes taxes & fees
8.6/10 Excellent! (2,715 reviews)
The hotel is great for families of all ages!

Reviewed on Apr 3, 2026

Hilton Chicago
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
500 South Dearborn Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,579 per night from Apr 5 to Apr 6
￥20,579
￥24,156 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (1,226 reviews)
I loved this hotel. Very classy, well decorated combining the historic aspects of the area with the buildings original high quality finishings and making it all look seamless. With that said, the view was only that of a nearby brick building but it did keep it much more quiet. They even had earplugs ...

Reviewed on Apr 2, 2026

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
See all 4,688 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 vacation package cost?
Starting from a low ￥105,900, a vacation 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 vacation 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 vacation?
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 vacation 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 vacation 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 vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.