Title: South Chicago Holidays 2026 from £1,135 | Expedia.co.uk

[Hotels in South Chicago](https://expedia.co.uk/South-Chicago-Chicago-Hotels.0-n6132199-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[South Chicago Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Chicago.d6132199.Car-Hire-Guide)

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# South Chicago Holidays from £1,135

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to £335 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Packages with flights are ATOL protected

### Your South Chicago Holiday

Booking a South Chicago holiday package is a wonderful way to become acquainted with this unique neighbourhood. From its must-visit places to its little-known delights, you won't be short of new adventures. Kick start your trip to South Chicago by visiting nearby attractions such as [Jackson Park](https://www.expedia.co.uk/Jackson-Park-Woodlawn.d507388.Attraction), [Calumet Park](https://www.expedia.co.uk/Calumet-Park-East-Side.d553248621555594792.Attraction) and [Calumet Beach](https://www.expedia.co.uk/Calumet-Beach-Chicago.d553248635983994343.Attraction). Stop daydreaming and start doing. When you're ready to book your dream holiday to South Chicago, Expedia will help get you there.

Price found within the past 48 hours. Click for updated prices.

![Sand Hill On The Lake](https://images.trvl-media.com/lodging/104000000/103140000/103131900/103131890/4e4e11d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sand Hill On The Lake

£1,135

per person

9 May - 16 May

found 1 day ago

Return flight included

London (LHR) to Chicago (ORD)

8.4/10 Very Good! (96 reviews)

The cottage is a beautiful room. Super quiet and peaceful. Only wish is that there was coffee mugs and some eating utensils. Forces you to not enjoy the room because you have to leave to get food or coffee but anyway I recommend this room. Very romantic.

Reviewed on 15 Feb 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

£1,516

per person

2 May - 9 May

found 1 day ago

Return direct flight included

London (LON) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Beautiful, amazing location, very clean, helpful staff, only negative was I was unable to purchase water after hours on site, had to make a quick walk to 7-Eleven.

Reviewed on 30 Mar 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

£1,816

per person

30 May - 6 Jun

found 17 hours ago

Return direct flight included

London (LON) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

Amazing experience will be back soon

Reviewed on 29 Mar 2026

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Magnificent Mile

Downtown Chicago

£1,722

per person

30 May - 6 Jun

found 17 hours ago

Return direct flight included

London (LON) to Chicago (ORD)

9/10 Wonderful! (3,314 reviews)

Great location. The staff was nice. It was everything we needed.

Reviewed on 29 Mar 2026

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Felix River North/Magnificent Mile

Downtown Chicago

£1,140

per person

2 May - 9 May

found 1 day ago

Return direct flight included

London (LON) to Chicago (ORD)

8.2/10 Very Good! (2,582 reviews)

Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!

Reviewed on 29 Mar 2026

## Where to stay in South Chicago

Find the best South Chicago areas and neighborhoods for the activities you enjoy most. [Learn more about South Chicago](https://expedia.co.uk/Chicago-South-Chicago.dx6132199)

![Downtown Chicago](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=6350699)

![Magnificent Mile](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

 Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. 

[Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=800025)

![The Loop](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(189 area reviews)

 Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. 

[Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=800024)

![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### O'Hare

3.5/5(10 area reviews)

 Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago. 

[Find hotels in O'Hare](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=553248635074842747)

![River North](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=6350695)

## Top hotels in South Chicago

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

£102

5 Apr - 6 Apr

includes taxes & fees

8/10 Very Good! (10,014 reviews)

N/A

Reviewed on 30 Mar 2026

[](https://expedia.co.uk/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6132199)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Fully refundableReserve now, pay when you stay

£121

5 Apr - 6 Apr

includes taxes & fees

9/10 Wonderful! (4,020 reviews)

Great location and great service

Reviewed on 30 Mar 2026

[](https://expedia.co.uk/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=6132199)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Fully refundableReserve now, pay when you stay

£126

12 Apr - 13 Apr

includes taxes & fees

8.6/10 Excellent! (5,799 reviews)

Pretty pricey for what you actually get. Valet is $79 per night on top of room fee. Beds are hard and uncomfortable. The linen on bed was full of stains. The temperature in room is either too hot or too cold. Pool water is disgusting. On the other hand:valet staff was excellent. The location is excellent. ...

Reviewed on 29 Mar 2026

[](https://expedia.co.uk/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6132199)

[See all 4,371 properties in South Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&regionId=6132199)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Holidays

[](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Holidays

[](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Friendly Holidays

[](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Holidays

[](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Holidays

[](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click)

![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ+ Holidays

[](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Holidays

[](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Holidays

[](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Pet Friendly Holidays

[](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click)

![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

## Frequently asked questions

### How much does a South Chicago travel package cost?

### If I'm not able to travel, can I cancel my South Chicago travel package?

### How do I get a cheap travel package to South Chicago?

### Does Expedia offer Book Now, Pay Later South Chicago holidays?

> - Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
> - Pay in instalments holidays: If you'd like to pay off your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
> - Low deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want.

### Where should I stay in South Chicago?

### What are the top hotels in South Chicago?

### How far in advance should I book my South Chicago holiday?

### What does an Expedia South Chicago travel package include?

### What should I know before booking a South Chicago travel package?

### Can I choose my airline with a South Chicago Expedia travel package?

### Popular places to visit

![Wrigley Field](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction)

![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction)

![Millennium Park](https://images.trvl-media.com/place/6069201/87d76a1e-e63f-48a2-8892-fb54ee86f8e1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

[](https://expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction)

### Things to do

![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 360 CHICAGO Observation Deck

£20

per adult

**86%** of travellers recommend

[](https://expedia.co.uk/things-to-do/360-chicago-observation-deck.a170348.activity-details)

![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago: Navy Pier Centennial Wheel Ticket

£18

per adult

**88%** of travellers recommend

[](https://expedia.co.uk/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wendella's 90-min Chicago River Architecture Tour

£30

per adult

**94%** of travellers recommend

[](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details)

[See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=6132199)

\* 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.