Near South Side Holidays from AU$2,747

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Your Near South Side Holiday

Lock in a holiday package to Near South Side and immerse yourself in everything this lakeside neighbourhood has to offer. Noted for its history, walking and culture, your next exciting adventure can be found right here. Start your trip to Near South Side by checking out nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help turn your ideal Near South Side holiday into reality, no matter your travel plans or budget.

Top Holiday Package Deals in Near South Side

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
per person
4 May - 10 May
found 7 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8/10 Very Good! (1,433 reviews)
I liked that the hotel was very close to all of the places we were going to, however I found the the hotel was in a tough spot when it came to finding parking. I did manage to find public parking just fine the side walk after driving around for 20 min.

Reviewed on 15 Feb. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
4 May - 10 May
found 7 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,550 reviews)
Wonderful check-in experience, slow weekend in Chicago I guess because I was given a wonderful upgrade. My room is as big as an apartment

Reviewed on 12 Feb. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 7 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (287 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on 20 Jan. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 7 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (998 reviews)
A very nice hotel. Good location with many restaurants in the area.

Reviewed on 14 Feb. 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
4 May - 10 May
found 7 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
I was upset that the elevators were not working and it took a long to get to my room and the lobby. I would have appreciated communication about this ahead of time and would have switched hotels. Apparently it had been an issue for at least two weeks. The staff were amazing. The rooms were dark and small.

Reviewed on 14 Feb. 2025

Our guide on 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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Our pick of the best 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 AU$158 per night from 17 Feb to 18 Feb
AU$158
includes taxes & fees
17 Feb - 18 Feb
7.8/10 Good! (8,473 reviews)
"The last day of my stay, a guy with a huge balloon in the shape of a rat was making a lot of noise with a speaker at the main door of the hotel, something very unpleasant. I don't understand why the hotel allowed that."

Reviewed on 12 Feb. 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 17 Feb to 18 Feb
AU$222
includes taxes & fees
17 Feb - 18 Feb
9.6/10 Exceptional! (1,627 reviews)
"all good"

Reviewed on 14 Feb. 2025

L7 Chicago by LOTTE
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$321 per night from 22 Feb to 23 Feb
AU$321
includes taxes & fees
22 Feb - 23 Feb
8.2/10 Very Good! (1,643 reviews)
"I look forward to staying again!"

Reviewed on 3 Feb. 2025

Hilton Chicago
See all 4,253 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Near South Side holiday package cost?
The most affordable Near South Side package is AU$2,747, so your dream holiday 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 holiday packages mean plenty of savings for the savvy traveller. 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 favourites among many travellers.
How far in advance should I book my Near South Side holiday?
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 holiday 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 holiday package?
We totally get it — life can throw you the odd curveball. If you’ve booked a Near South Side holiday 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

McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Soldier Field featuring a city, modern architecture and a high-rise building

Soldier Field

4/5(13 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Adler Planetarium and Astronomy Museum featuring modern architecture

Adler Planetarium and Astronomy Museum

4/5(1 review)

Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.

Adler Planetarium and Astronomy Museum

Activities

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

AU$207
per adult
78% of travellers recommend
Chicago Pass: Save up to 50 Percent - Includes 360 Chicago
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

AU$66
per adult
Field Museum of Natural History All-Access Pass
Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

AU$90
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
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.