Near South Side Holidays from £851
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Near South Side Holiday
Book a holiday package to Near South Side and get set to immerse yourself in its history, walking and culture. However you want to spend your time in this lakeside neighbourhood, there are plenty of opportunities for relaxation and fun. Your trip to Near South Side wouldn't be complete without stopping by leading attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Don't just dream it — turn it into reality! Secure your ideal Near South Side holiday with Expedia and enjoy travelling your way.
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
£2,409
per person
12 Nov - 16 Nov
found 4 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Overall great place to stay; the only odd thing was housekeeping knocked on our door at 9:15 at night which we weren't expecting. Otherwise it was quiet, comfortable and a great location to get to everything.
Reviewed on 17 Sept 2026
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
4 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Near South Side
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
£286
8 Oct - 9 Oct
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£165
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (5,435 reviews)
"Brken elevator, no fridge very small room, king bed was a split mattress that I kept slipping into the Crack. Very displeased for the ridiculous high price paid."
Reviewed on 17 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£159
13 Oct - 14 Oct
includes taxes & fees
8/10 Very good! (2,256 reviews)
"Room was filthy. Hallway was dirty. Staff was nice. My room wasn’t cleaned daily and wasn’t the cleanest when I arrived."
Reviewed on 17 Sept 2026
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 travel package cost?
Explore the best of Near South Side from just £851. Choose from a wonderful selection of flights, hotels and rental cars to suit every budget. You can score even more discounts when you add a few activities or tours to your travel package.
If I'm not able to travel, can I cancel my Near South Side travel package?
We totally understand — life can throw you the odd curveball. If you've booked a Near South Side travel package and need to amend or cancel it, we're here to help. It's always worth taking a look at our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.
How do I get a cheap travel package to Near South Side?
Combine your hotel and flight bookings, add on extras such as activities or a rental car, and save with a Near South Side travel package. You won't just enjoy wonderful discounts on your adventure — you'll have a world of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 hotels throughout the world. Your unforgettable holiday begins right here, right now!
Does Expedia offer Book Now, Pay Later Near South Side holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that works for you during the checkout process and take the stress out of budgeting for your next trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:
- Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's monthly instalment plans. If paying bite-sized amounts each month works for you, pick this option during the checkout process.
- Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.
Where should I stay in Near South Side?
Urban adventurers come from all over the world to see Millennium Park and Wrigley Field in Near South Side. Book yourself a room close to these terrific attractions to make sightseeing a breeze.
What are the top hotels in Near South Side?
If it's your first visit to Near South Side, reserve a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both offer friendly service and are top options with many savvy travellers.
How far in advance should I book my Near South Side holiday?
Travellers are generally able to look up international fares on Expedia up to a year in advance of departure. Booking late? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your journey.
What does an Expedia Near South Side travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your dream Near South Side holiday. You can also add on experiences and activities once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score discounts you won't find anywhere else.
What should I know before booking a Near South Side travel package?
You'll land great savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one spot simply makes planning easier. So why waste money or time? Whether you're putting together a ritzy romantic getaway or a low-cost family break, take a look at our package deals today.
Can I choose my airline with a Near South Side Expedia travel package?
Yes — that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 airline partners across the globe, so you have lots of choice when putting together your Near South Side trip.
Stay near popular Near South Side attractions
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 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.
Photo by City Of Chicago
Field Museum of Natural History
9.4/10 (1,744 reviews)
Dinosaur bones, rare gems and real Egyptian mummies are among the displays at this family favorite.
Adler Planetarium and Astronomy Museum
8.8/10 (248 reviews)
Opportunities for fun, learning and wonder abound at this historic and state-of-the-art museum on the pretty shore of Lake Michigan.
Northerly Island Natural Area
8.6/10 (28 reviews)
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
Commune with nature and explore the great outdoors at Northerly Island during your travels in Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.
Wintrust Arena
8.0/10 (70 reviews)
Catch an event at Wintrust Arena during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
Arie Crown Theater
8.0/10 (9 reviews)
You can get tickets for a performance at Arie Crown Theater during your stay in Chicago. Experience the fascinating museums and acclaimed art galleries in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.