Near South Side Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Lobby lounge
    Aug 14 - Aug 16

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Would definitely stay here again! Clean, friendly staff, great location."
    Reviewed May 23, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$999
    NZ$787
    per traveller
    found 1 day ago
    Le Méridien Essex Chicago
  • Lobby
    Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,717 reviews)
    "Too small room no refrigerator no microwave over prized vallet parking when they park in open public parking space which cost less."
    Reviewed May 23, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,164
    NZ$878
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Executive lounge
    Aug 14 - Aug 16

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    8.8/10 - Excellent (2,165 reviews)
    "Amazing staff. Clean rooms!"
    Reviewed May 21, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,127
    NZ$859
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park
  • 55-inch LCD TV with cable channels, TV, pay films
    Aug 14 - Aug 16

    L7 Chicago by LOTTE + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.6/10 - Exceptional (4,081 reviews)
    "Upon check-in, Alex was kind and helpful. He gave us some great tips about the hotel and some things to explore and where to eat. Alex was moved by our mother-daughter trip before my daughter travels to Spain to study. He even left us a sweet treat which was a perfect end to our evening. The room, the view, and the shower were absolutely perfect! We will be back to Chicago and because of Alex we will only be staying at L7 when we do. Thanks for your kind words, Alex."
    Reviewed May 24, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,106
    NZ$885
    per traveller
    found 1 day ago
    L7 Chicago by LOTTE
  • Indoor wedding
    Aug 14 - Aug 16

    Swissotel - Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.0/10 - Wonderful (3,337 reviews)
    "Great location!"
    Reviewed May 23, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,201
    NZ$964
    per traveller
    found 1 day ago
    Swissotel - Chicago

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

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

Our pick of the best Near South Side Hotel Deals

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$516 per night from 26 May to 27 May
NZ$516
26 May - 27 May
includes taxes & fees
9.2/10 Wonderful! (1,077 reviews)
"knotted door and asked what time would be left when I was sleeping"

Reviewed on 23 May 2026

Hyatt Regency McCormick Place Chicago
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 NZ$271 per night from 25 May to 26 May
NZ$271
25 May - 26 May
includes taxes & fees
Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$317 per night from 25 May to 26 May
NZ$317
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,220 reviews)
"Clean room good breakfast"

Reviewed on 24 May 2026

Hotel Riu Plaza Chicago
See all 4,670 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 holiday package cost?
The most affordable Near South Side package is , 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
Field Museum of Natural History

Field Museum of Natural History

4.5/5(9 reviews)

Explore hidden worlds, ancient secrets, and bizarre creatures – and a dinosaur terror named Sue.

Field Museum of Natural History
Adler Planetarium and Astronomy Museum

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.