Near South Side Holidays from £820

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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.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on 10 Jan 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Good location, nice vibe, amazing staff!

Reviewed on 30 Apr 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (1,056 reviews)
Very nice Hotel in the best location

Reviewed on 2 May 2024

Kimpton Hotel Monaco Chicago, an IHG Hotel

Kimpton Hotel Monaco Chicago, an IHG Hotel

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Nice neighborhood with great restaurant close by. Style of hotel was cool with window seat, great views.

Reviewed on 29 Apr 2024

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,649 reviews)
Friend took the subway to see me. Was walkable to other areas and had a nice pool.

Reviewed on 2 May 2024

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

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 £133 per night from 13 May to 14 May
£133
per night
13 May - 14 May
7.6/10 Good! (6,636 reviews)
"I loved my stay at the Congress Plaza Hotel! Check in was easy, especially since I got to check in at 12 noon, instead of 3PM. My room was very spacious and my king size bed was made up nicely and it was very comfortable too! There were plenty of towels in the pretty bathroom. The flatscreen TV was ..."

Reviewed on 1 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £150 per night from 12 May to 13 May
£150
per night
12 May - 13 May
8.6/10 Excellent! (2,834 reviews)
"Loved the free water. Hotel staff (Pedro) was very friendly & helpful! The room was the perfect size for one person."

Reviewed on 30 Apr 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £159 per night from 12 May to 13 May
£159
per night
12 May - 13 May
8.2/10 Very Good! (1,876 reviews)
","

Reviewed on 29 Apr 2024

Eurostars Magnificent Mile
See all 4,101 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 £820. 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.

Popular places to visit

Image for McCormick Place

McCormick Place

4.5/5(36 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
Image for Soldier Field

Soldier Field

4/5(44 reviews)

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

Soldier Field
Image for Shedd Aquarium

Shedd Aquarium

4.5/5(29 reviews)

Make time in your itinerary to visit the sea life who live at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Shedd Aquarium

Things to do

Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

£81
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
Image for Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

£32
Per adult
Field Museum of Natural History All-Access Pass
Image for Field Museum of Natural History Ticket with Self-Guided Audio Tour

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

£38
Per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
See all activities in Chicago

More trip options

* 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.