Near South Side Holidays from £720

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £944, price is now £720 per person
£720
per person
14 Jan - 21 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,099, price is now £793 per person
£793
per person
14 Jan - 21 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,318, price is now £977 per person
£977
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
The room was Actually very clean. Staff was very nice with patient & polite. Nice view. Plenty of restaurants and stuff to do. I would Definitely suggest valet parking $76 in & out because self parking is $65 with no in & out.

Reviewed on 2 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,477, price is now £1,127 per person
£1,127
per person
5 Jan - 12 Jan
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,333, price is now £1,019 per person
£1,019
per person
5 Jan - 12 Jan
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Very beautiful room with great view... no complaints

Reviewed on 1 Nov 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
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago

Top hotels in Near South Side

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 £103 per night from 10 Nov to 11 Nov
£103
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,094 reviews)
"This was an older hotel but very well maintained. I stayed here with my two daughters (19 & 13) and it was spacious enough for us three. We were able to see the fireworks at the pier from our room."

Reviewed on 3 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £103 per night from 4 Nov to 5 Nov
£103
4 Nov - 5 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £99 per night from 26 Nov to 27 Nov
£99
26 Nov - 27 Nov
includes taxes & fees
River Hotel
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Near South Side travel package cost?
Explore the best of Near South Side from just £720. 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

A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.