Title: South Side Vacation Packages 2026 from $485 | Expedia.com

[South Side Travel Guide](https://expedia.com/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.com/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.com/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.com/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.com/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[Car Rentals in South Side](https://expedia.com/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# South Side Vacations from $485

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

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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Plan, book, and manage your trip all in one place

## The Latest South Side vacation packages

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

![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

$485

per person

Jun 12 - Jun 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (3,688 reviews)

Very beautiful hotel! Room was spacious and clean and great front desk service, especially Francisco he was very nice and even let me check in early..which was greatly appreciated.

Reviewed on Apr 8, 2026

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$845

per person

Jun 11 - Jun 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (3,647 reviews)

Very nice and clean hotel

Reviewed on Apr 8, 2026

![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8920c075_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Thompson Chicago, by Hyatt

Downtown Chicago

Save 100% on your flight

$1,008

per person

Jun 11 - Jun 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,332 reviews)

Restaurant next door can be loud and surprise you when entering the lobby. Great location. Will return.

Reviewed on Apr 8, 2026

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

$537

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,241 reviews)

Great location and service. Needs alittle renovation of interior

Reviewed on Apr 7, 2026

![Hotel Saint Clair- Magnificent Mile](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/c230295e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$685

per person

Jun 25 - Jun 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (1,881 reviews)

Good location , room was small clean. They were sold out of rooms with refrigerators and weren’t very accommodating on moving me when one became available. Staff makes quite the noise in the morning time but overall it was a decent stay ..

Reviewed on Apr 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to South Side

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-09/2026-05-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. [Learn more about South Side](https://expedia.com/South-Side.dx553248635074842823)

![Hyde Park](https://images.trvl-media.com/place/6064043/29f0986c-b49b-485b-8fcc-9b5424ca802f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Hyde Park

4 out of top 10 points of interest in this area

4.5/5(136 area reviews)

 Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan. 

[Find hotel + flight trips in Hyde Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Hyde%20Park&DestID=117842&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![EyeEm Custom Shoots Q4 2018](https://images.trvl-media.com/place/6003647/e3f94976-3603-43a7-a36a-570792654b8d.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Chinatown

4/5(204 area reviews)

 If you're spending time in Chinatown, you might enjoy attractions like South Wentworth Street and Chinese American Museum of Chicago. You might also enjoy the neighborhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city. 

[Find hotel + flight trips in Chinatown](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Chinatown&DestID=6003647&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![www.alamy.com](https://images.trvl-media.com/place/6132075/cfd0936f-7a46-4712-9bcf-9fc886479e02.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Bridgeport

4/5(1 area review)

 Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Bridgeport Art Center and Zhou B Art Center, and jump on the metro at Halsted Station (Orange Line) to get around the city. 

[Find hotel + flight trips in Bridgeport](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bridgeport&DestID=6132075&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Bronzeville Bridge ](https://images.trvl-media.com/place/6132245/bdf0ca23-8e04-4a02-a6f8-aaeeeaf14c16.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Bronzeville

1 out of top 10 points of interest in this area

3.5/5(294 area reviews)

 Travelers choose Bronzeville for its abundant dining options. Hop aboard the metro at 35th-Bronzeville-IIT Station or Indiana Station and check out top sights like Lake Michigan. 

[Find hotel + flight trips in Bronzeville](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bronzeville&DestID=6132245&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Aerial Chicago Douglas Neighborhood](https://images.trvl-media.com/place/6132367/ef7d8028-54cc-4a3b-8ea2-51bfd9daba05.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Douglas

1 out of top 10 points of interest in this area

 Visitors often come to Douglas for its abundant dining options, but many stay to explore sights like Lake Michigan and McCormick Tribune Center. Getting around the area on the metro is easy if you catch a ride at 35th-Bronzeville-IIT Station. 

[Find hotel + flight trips in Douglas](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Douglas&DestID=6132367&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

### Discover the most popular places to visit in South Side

![Aerial View of a large University in the Chicago Neighborhood of Hyde Park](https://images.trvl-media.com/place/6064081/ed547d2b-1357-42b3-840a-f88661f7db9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### University of Chicago

4.5/5(1,186 reviews)

Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area. 

[](https://expedia.com/University-Of-Chicago-Hyde-Park.d6064081.Vacation-Attraction)

![Griffin Museum of Science and Industry](https://images.trvl-media.com/place/6064043/29f0986c-b49b-485b-8fcc-9b5424ca802f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Griffin Museum of Science and Industry

4.5/5(1,396 reviews)

This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

[](https://expedia.com/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)

![Jackson Park](https://images.trvl-media.com/place/829/43e5e7c2-f359-41d5-bf37-c86a2ac41010.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Jackson Park

4/5(7 reviews)

Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums. 

[](https://expedia.com/Jackson-Park-Woodlawn.d507388.Vacation-Attraction)

### What to do in South Side

![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

$27

per adult

**86%** of travellers recommend

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

![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Bulls Basketball Game at United Center

$66

per adult

**80%** of travellers recommend

[](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flyover in Chicago

$38

per adult

**98%** of travellers recommend

[](https://expedia.com/things-to-do/flyover-in-chicago.a50023979.activity-details)

[See all activities in South Side](https://expedia.com/things-to-do/search?rid=553248635074842823)

## South Side Hotel Deals

![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Fully refundable

$113 nightly

$131 total

May 10 - May 11

Total with taxes and fees

8.4/10 Very Good! (999 reviews)

Stuff very professional and helpful!!!!

Reviewed on Apr 8, 2026

[](https://expedia.com/Hotel-Search?startDate=5%2F10%2F2026&endDate=5%2F11%2F2026&selected=2190&PinnedHotelID=2190&HadPinnedHotel=true&regionId=553248635074842823)

![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Jaslin Hotel

261 West Cermak Rd Chicago IL

Fully refundableReserve now, pay when you stay

$107 nightly

$126 total

Apr 28 - Apr 29

Total with taxes and fees

9/10 Wonderful! (1,198 reviews)

All staff was polite, room was clean. Would be a great convenience if there was a microwave in the room and a hair dryer.

Reviewed on Apr 8, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F28%2F2026&endDate=4%2F29%2F2026&selected=13320264&PinnedHotelID=13320264&HadPinnedHotel=true&regionId=553248635074842823)

![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE Chicago IL

Fully refundableReserve now, pay when you stay

$134 nightly

$157 total

Apr 15 - Apr 16

Total with taxes and fees

9.6/10 Exceptional! (1,006 reviews)

Overall excellent

Reviewed on Apr 8, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F15%2F2026&endDate=4%2F16%2F2026&selected=64624399&PinnedHotelID=64624399&HadPinnedHotel=true&regionId=553248635074842823)

[See all 475 properties in South Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F10%2F2026&endDate=4%2F11%2F2026&regionId=553248635074842823)

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.

## Find the Best South Side Vacation Packages

## South Side Essential Information

| Language        | English                    |
| --------------- | -------------------------- |
| Currency        | U.S dollars                |
| Closest Airport | O'Hare Intl. Airport (ORD) |

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- [Cheap Hotels in Hyde Park ](https://www.expedia.com/Hyde-Park-Chicago-Hotels-Cheap-Hotels.0-n117842-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hilton Hotels in Hyde Park ](https://www.expedia.com/Hyde-Park-Chicago-Hotels-Hilton-Hotels.0-n117842-0--bHiltonHotels.Travel-Guide-Filter-Hotels)
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- [Marriott Hotels & Resorts in Hyde Park ](https://www.expedia.com/Hyde-Park-Chicago-Hotels-Marriott-Hotels-Resorts.0-n117842-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Hotels near Chicago 47th Street Station ](https://www.expedia.com/Chicago-47th-Street-Station-Hotels.d6212783.Travel-Guide-Hotels)
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- [Hotels near DuSable Museum of African-American History ](https://www.expedia.com/DuSable-Museum-Of-African-American-History-Hotels.0-l6065113-0.Travel-Guide-Filter-Hotels)
- [Hyatt Hotels in Hyde Park ](https://www.expedia.com/Hyde-Park-Chicago-Hotels-Hyatt-Hotels.0-n117842-0--bHyattHotels.Travel-Guide-Filter-Hotels)
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- [Hotels with an Indoor Pool in Hyde Park ](https://www.expedia.com/Hyde-Park-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n117842-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
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- [Flights to Chicago ](https://www.expedia.com/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
- [Flights from Chicago ](https://www.expedia.com/lp/flights/178248/flights-from-chicago)

- [Chicago Vacations ](https://www.expedia.com/Chicago.d178248.Destination-Travel-Guides)
- [Obama's House ](https://www.expedia.com/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction)
- [Kam Synagogue ](https://www.expedia.com/KAM-Synagogue-Kenwood.d553248621533116332.Vacation-Attraction)
- [4944 S Woodlawn Ave ](https://www.expedia.com/4944-S-Woodlawn-Ave-Kenwood.d553248621533116335.Vacation-Attraction)
- [Griffin Museum of Science and Industry ](https://www.expedia.com/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Elijah Muhammad House ](https://www.expedia.com/Elijah-Muhammad-House-Kenwood.d553248621533116336.Vacation-Attraction)
- [Visit Washington Park Court ](https://www.expedia.com/Chicago-Washington-Park-Court.dx6132200)
- [Smart Museum of Art ](https://www.expedia.com/Smart-Museum-Of-Art-Hyde-Park.d6064071.Vacation-Attraction)
- [Muddy Waters’ House ](https://www.expedia.com/Muddy-Waters-House-Kenwood.d553248621533116347.Vacation-Attraction)
- [Dusable Museum of African-American History ](https://www.expedia.com/DuSable-Museum-Of-African-American-History-Washington-Park.d6065113.Vacation-Attraction)
- [Hyde Park Vacations ](https://www.expedia.com/Hyde-Park.d117842.Destination-Travel-Guides)
- [Hyde Park Hair Salon ](https://www.expedia.com/Hyde-Park-Hair-Salon-Hyde-Park.d553248621533116334.Vacation-Attraction)
- [Robie House ](https://www.expedia.com/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)
- [Visit Grand Boulevard ](https://www.expedia.com/Chicago-Grand-Boulevard.dx6132310)
- [University of Chicago ](https://www.expedia.com/University-Of-Chicago-Hyde-Park.d6064081.Vacation-Attraction)
- [Visit Kenwood ](https://www.expedia.com/Chicago-Kenwood.dx6132343)
- [Midway Plaisance ](https://www.expedia.com/Midway-Plaisance-Hyde-Park.d6069199.Vacation-Attraction)
- [Visit Hyde Park ](https://www.expedia.com/Chicago-Hyde-Park.dx117842)
- [Rockefeller Memorial Chapel ](https://www.expedia.com/Rockefeller-Memorial-Chapel-Hyde-Park.d553248621533116328.Vacation-Attraction)

- [Car rentals near Chicago ](https://www.expedia.com/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)
- [Car rentals near 4944 S Woodlawn Ave ](https://www.expedia.com/Car-Rentals-In-4944-S-Woodlawn-Ave.d553248621533116335.Car-Rental-Guide)
- [Car rentals near Hyde Park ](https://www.expedia.com/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide)
- [Enterprise Rental Cars in Hyde Park ](https://www.expedia.com/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers)
- [Hertz Rental Cars in Hyde Park ](https://www.expedia.com/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers)
- [Budget Rental Cars in Hyde Park ](https://www.expedia.com/Budget-Car-Rentals-In-Hyde-Park.d117842-c39.Car-Rental-Guide-Suppliers)
- [Avis Rental Cars in Hyde Park ](https://www.expedia.com/Avis-Car-Rentals-In-Hyde-Park.d117842-c41.Car-Rental-Guide-Suppliers)
- [Rent A Wreck Rental Cars in Hyde Park ](https://www.expedia.com/Rent-A-Wreck-Car-Rentals-In-Hyde-Park.d117842-c33.Car-Rental-Guide-Suppliers)
- [National Car Rental Rental Cars in Hyde Park ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Hyde-Park.d117842-c42.Car-Rental-Guide-Suppliers)
- [Van Car Rentals in Hyde Park ](https://www.expedia.com/Van-Car-Rentals-In-Hyde-Park.d117842-tVan.Car-Rental-Guide-Class)
- [First-Car Rental Cars in Hyde Park ](https://www.expedia.com/First-Car-Car-Rentals-In-Hyde-Park.d117842-c1019.Car-Rental-Guide-Suppliers)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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