Near South Side Vacations from NT$17,606

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The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$30,865, price is now NT$17,606 per person
NT$17,606
per person
May 25 - May 29
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Great stay! Loved to come back. Friendly staff!

Reviewed on 2026/4/13

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,938, price is now NT$42,237 per person
NT$42,237
per person
May 25 - May 29
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 2026/4/7

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$28,178, price is now NT$19,788 per person
NT$19,788
per person
May 25 - May 29
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
8.4/10 Very Good! (1,881 reviews)
Rooms are small but clean. Beds comfortable. Tiny bathroom but it still has a walk in shower. Street noise with often sirens due to hospital proximity. Pricing was appropriate for the space. Adequate for a brief stay at NMH.

Reviewed on 2026/4/14

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$36,095, price is now NT$25,608 per person
NT$25,608
per person
May 25 - May 29
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 2026/4/14

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$26,698, price is now NT$19,350 per person
NT$19,350
per person
May 25 - May 29
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Clean and comfortable

Reviewed on 2026/4/14

Where to stay in Near South Side

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

Near South Side 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 NT$3,921 per night from Apr 26 to Apr 27
NT$3,921
NT$4,604 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,144 reviews)
We stayed here in order to be close to the Auditorium for our concert. The price is great, but you get what you pay for. It was very average, which isn't a bad thing necessarily. My only big comlaint is the lack of individualized climate control. There is a unit and you are at the mercy of whatever ...

Reviewed on 2026/4/14

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,360 per night from Apr 26 to Apr 27
NT$4,360
NT$5,118 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,133 reviews)
Hotel was close to the Mile and attractions. Facilities in good condition, somewhat aged, Do no expect an impressive an inviting Lobby and Lounge. Side Bar was expensive for what it offered. Space was clean and staff attentive. Suite was of OK dimensions. Room TV's were old but functional. Shower ...

Reviewed on 2026/4/14

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is NT$4,929 per night from Apr 28 to Apr 29
NT$4,929
NT$5,786 total
Apr 28 - Apr 29
includes taxes & fees
8.6/10 Excellent! (5,838 reviews)
The sheets were dirty and in the lobby it was dog poop

Reviewed on 2026/4/14

Embassy Suites by Hilton Chicago Downtown River North
See all 4,706 properties in Near South Side
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 Near South Side vacation package cost?
The most affordable Near South Side package is NT$17,606, so your dream vacation can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to custom build a package that suits your travel style.
How do I get a cheap travel package to Near South Side?
Our Near South Side vacation packages mean plenty of savings for the savvy traveler. For the best deal, simply bundle your hotel, flights and extras (such as activities) into a budget-friendly package. But cheap prices are only the start of your next big adventure. Book with Expedia and you'll have more than 550 airlines and 1,000,000 hotels all over the world to choose from. Whatever your style or budget, there's a package here just for you.
Where should I stay in Near South Side?
Most who travel to Near South Side put both McCormick Place and Millennium Park on their to-do lists. Why not select a hotel within walking distance of these great attractions?
What are the top hotels in Near South Side?
If it's your first visit to Near South Side, lock in a room at Sonder South Wabash or Hotel BnB. Both hotels will make you feel at home and are favorites among many travelers.
How far in advance should I book my Near South Side vacation?
It all depends on the airline, but you can normally compare international flights on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky customers occasionally nab a cheaper flight just weeks prior to their intended journey.
What does an Expedia Near South Side travel package include?
Choose from a combination of flights, hotels and rental cars. Once you've made your booking, you can add some experiences and tours. Want to pick your fare class? That's easily done too. The choice is yours when it comes to crafting your dream Near South Side escape.
What should I know before booking a Near South Side travel package?
Tailor deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we've got everything you need to plan your getaway. You'll save big bucks just by bundling your bookings. Whether you're embarking on a winter adventure or sunning yourself on a warm beach, your ideal getaway is only a few clicks away.
Can I choose my airline with a Near South Side Expedia vacation package?
Yes, the choice is yours. We offer more than 550 partner airlines globally, so you can tailor your Near South Side escape according to your budget and style.
If I'm not able to travel, can I cancel my Near South Side vacation package?
We totally get it — life can throw you the odd curveball. If you've booked a Near South Side vacation package and need to cancel or change it, we can help. It's always worth checking out our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to change your itinerary for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a fee.

Discover the most popular places to visit in Near South Side

Lakefront Trail

Lakefront Trail

4.5/5(50 reviews)

Lakefront Trail is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Wander the lakeside and beautiful beaches in the area.

Lakefront Trail
Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

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