Near South Side Holidays from £1,469

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,133, price is now £1,469 per person
£1,469
per person
11 Jul - 18 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,228, price is now £1,480 per person
£1,480
per person
11 Jul - 18 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Breakfasr good, view great

Reviewed on 1 May 2026

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 £2,411, price is now £1,692 per person
£1,692
per person
11 Jul - 18 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
I loved it. The location was perfect and I specifically pick this hotel based on the view and it did not disappoint. If you don’t wanna go far, there are plenty of restaurants and things to do right around the hotel so that was also convenient. I will definitely be going back.

Reviewed on 1 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,883, price is now £2,043 per person
£2,043
per person
11 Jul - 18 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back

Reviewed on 27 Apr 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,247, price is now £1,642 per person
£1,642
per person
11 Jul - 18 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Overall, my stay at LondonHouse was good. The location is excellent, the hotel is clean, and the staff are polite. However, there were a few downsides. I tried to go to the rooftop several times, but each time I was told it was closed because I wasn’t planning to order food. That didn’t feel right and seemed like access was unnecessarily restricted. Also, the bedsheets were not changed unless I specifically requested it, which is below expectations for a hotel at this level. Another issue was that there was no microwave anywhere in the hotel. Even having one per floor would have been very helpful. Overall, it’s a good hotel, but these points could definitely improve the guest experience.

Reviewed on 30 Apr 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

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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £98 per night from 25 May to 26 May
£98
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,656 reviews)
I never made it to hotel due to airline canceling flight. The hotel would not give me full refund for something that was out of my control. I WOULD NEVER BOOK WITH THIS HOTEL AGAIN. there should be courtesy given when your flight is canceled and you have no way to get there.

Reviewed on 1 May 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 26 May to 27 May
£118
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,148 reviews)
Room was a little small but worked out perfect! Great location.

Reviewed on 2 May 2026

River Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 10 May to 11 May
£136
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (4,245 reviews)
I don’t understand the excellent reviews at this hotel. The hotel was in a great location. However the room was very dated and smelled of mildew and mold. Shower was filthy. Furniture was falling apart. Would not stay here again.

Reviewed on 2 May 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,671 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.
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Frequently asked questions

How much does a Near South Side travel package cost?
Explore the best of Near South Side from just £1,469. 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

Elbridge G Keith House

Learn about the local history of Chicago with a stop at Elbridge G Keith House. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Elbridge G Keith House

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.