Title: South Loop Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $747 Expedia.ca

[South Loop Travel Guide](https://expedia.ca/Chicago-South-Loop.dx6130108)[Hotels in South Loop](https://expedia.ca/South-Loop-Chicago-Hotels.0-n6130108-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[South Loop Car Rentals](https://expedia.ca/Car-Rentals-In-South-Loop.d6130108.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6130108/f1bd0360-1400-4c1c-882e-1779972b657f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# South Loop Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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  
Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in South Loop

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

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $747

per person

Mar 14 - Mar 17

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Clean rooms & courteous staff

Reviewed on Dec 25, 2025

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $765

per person

Mar 14 - Mar 17

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,097

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Excellent! Everything was perfect, beautiful and the staff are amazing!

Reviewed on Dec 27, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,243

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

They went above and beyond! Perfect stay!

Reviewed on Dec 26, 2025

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $776

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Room was really clean and fresh

Reviewed on Dec 27, 2025

## Where to stay in South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. [Learn more about South Loop](https://expedia.ca/Chicago-South-Loop.dx6130108)

![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.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 hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

 Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. 

[Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(725 area reviews)

 Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. 

[Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### River North

 Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. 

[Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Chicago which includes rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Theatre District

 While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line). 

[Find hotel + flight trips in Theatre District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Theatre%20District&DestID=651190586167894016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## South Loop Hotel Deals

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $167

CA $236 total

Jan 2 - Jan 3, 2026

includes taxes & fees

8.4/10 Very Good! (2,412 reviews)

What a great stay!!

Reviewed on Dec 24, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F01%2F2026&endDate=03%2F01%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true&regionId=6130108)

![Homewood Suites by Hilton Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2d5c8626_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Homewood Suites by Hilton Chicago Downtown South Loop

59 E. 11th Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $111

CA $130 total

Jan 5 - Jan 6, 2026

includes taxes & fees

8.6/10 Excellent! (2,160 reviews)

While the room itself was great, we were somewhat disappointed in the continental breakfast experience as a whole. There were many items not available. By the time we waited for the hot items to come out, the food we were able to get was cold. There was also no seating available so we had to take ...

Reviewed on Dec 24, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=33387384&PinnedHotelID=33387384&HadPinnedHotel=true&regionId=6130108)

![Hilton Garden Inn Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Garden Inn Chicago Downtown South Loop

55 E 11th Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $103

CA $121 total

Jan 5 - Jan 6, 2026

includes taxes & fees

8.6/10 Excellent! (1,771 reviews)

The staff were all very helpful. Location was convenient for our stay and the view of the city from our room was amazing! The entire hotel was very clean also.

Reviewed on Dec 20, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=33682469&PinnedHotelID=33682469&HadPinnedHotel=true&regionId=6130108)

[See all 4,733 properties in South Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&regionId=6130108)

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 Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

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

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a South Loop vacation package cost?

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

### Where should I stay in South Loop?

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

### How far in advance should I book my South Loop vacation?

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

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

### Can I choose my airline with a South Loop Expedia vacation package?

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

### Things to do

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

CA $44

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details)

![Chicago's Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/48840807/49f0c7f9-d7f7-4281-a580-006a5c5fd53f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago's Navy Pier Centennial Wheel Ticket

CA $33

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/chicagos-navy-pier-centennial-wheel-ticket.a48840807.activity-details)

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6130108)

## Explore a world of travel with Expedia

- Lodging
- Flights
- Packages
- Cars
- Other

- [Hotels near Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels)
- [Hotels near Burnham Park ](https://www.expedia.ca/Burnham-Park-Hotels.0-l6182814-0.Travel-Guide-Filter-Hotels)
- [Family Hotels in Central Station ](https://www.expedia.ca/Central-Station-Chicago-Hotels-Family-Hotel.0-n6132250-0-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Central Station ](https://www.expedia.ca/Central-Station-Chicago-Hotels-Luxury-Hotel.0-n6132250-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in Central Station ](https://www.expedia.ca/Central-Station-Chicago-Hotels-Romantic-Hotel.0-n6132250-0-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [Central Station Hotels ](https://www.expedia.ca/Central-Station-Chicago-Hotels.0-n6132250-0.Travel-Guide-Filter-Hotels)
- [Aparthotels in Cermak-Chinatown Station ](https://www.expedia.ca/Cermak-Chinatown-Station-Apart-Hotels.d6210889-aaApartHotels.Travel-Guide-Accommodation)
- [Hotels near Cermak-Chinatown Station ](https://www.expedia.ca/Cermak-Chinatown-Station-Hotels.d6210889.Travel-Guide-Hotels)
- [Hotels near Cermak-McCormick Place Station ](https://www.expedia.ca/Cermak-McCormick-Place-Station-Hotels.d553248635996309411.Travel-Guide-Hotels)
- [Hotels near Chicago 18th Street Station ](https://www.expedia.ca/Chicago-18th-Street-Station-Hotels.d6212763.Travel-Guide-Hotels)
- [Cheap Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Cheap-Hotels.0-0-d178248-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Marriott Hotels & Resorts in Chicago ](https://www.expedia.ca/Chicago-Hotels-Marriott-Hotels-Resorts.0-0-d178248--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Chicago Hotels ](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)
- [Hotels near Chicago Museum Campus-11th Street Station ](https://www.expedia.ca/Chicago-Museum-Campus-11th-Street-Station-Hotels.d6212755.Travel-Guide-Hotels)
- [Inns in Chicago Museum Campus-11th Street Station ](https://www.expedia.ca/Chicago-Museum-Campus-11th-Street-Station-Inns.d6212755-aaInns.Travel-Guide-Accommodation)
- [All Inclusive Resorts and in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-All-Inclusive-Hotel.0-n6175487-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Best Western Hotels in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-Best-Western.0-n6175487-0--bBestWestern.Travel-Guide-Filter-Hotels)
- [Business Hotels in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-Business-Hotel.0-n6175487-0-tBusinessHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-Cheap-Hotels.0-n6175487-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-Historic-Hotel.0-n6175487-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hotels with a Pool in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-Hotel-With-Pool.0-n6175487-0-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Chicago Museum Campus ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels-Luxury-Hotel.0-n6175487-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Chicago Museum Campus Hotels ](https://www.expedia.ca/Chicago-Museum-Campus-Chicago-Hotels.0-n6175487-0.Travel-Guide-Filter-Hotels)
- [All Inclusive Resorts and in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-All-Inclusive-Hotel.0-n6003647-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Business Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Business-Hotel.0-n6003647-0-tBusinessHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Cheap-Hotels.0-n6003647-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Family Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Family-Hotel.0-n6003647-0-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Historic-Hotel.0-n6003647-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Early Check-in in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Hotel-With-Early-Check-In.0-n6003647-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Luxury-Hotel.0-n6003647-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Pet-Friendly-Hotel.0-n6003647-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Red Roof Inn Hotels in Chinatown ](https://www.expedia.ca/Chinatown-Chicago-Hotels-Red-Roof-Inn.0-n6003647-0--bRedRoofInn.Travel-Guide-Filter-Hotels)
- [Chinatown Hotels ](https://www.expedia.ca/Chinatown-Chicago-Hotels.0-n6003647-0.Travel-Guide-Filter-Hotels)
- [Hotels near Dearborn St Station ](https://www.expedia.ca/Dearborn-St-Station-Hotels.0-l553248621533116535-0.Travel-Guide-Filter-Hotels)
- [Downtown Chicago Hotels ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels)
- [Hotels near Field Museum of Natural History ](https://www.expedia.ca/Field-Museum-Of-Natural-History-Hotels.0-l6065115-0.Travel-Guide-Filter-Hotels)
- [Hotels near Grant Park ](https://www.expedia.ca/Grant-Park-Hotels.0-l507389-0.Travel-Guide-Filter-Hotels)
- [Hotels near Lollapalooza ](https://www.expedia.ca/Lollapalooza-Hotels.0-l553248635977254161-0.Travel-Guide-Filter-Hotels)
- [Magnificent Mile Hotels ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels)
- [Hotels near McCormick Place ](https://www.expedia.ca/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels)
- [Hotels near Millennium Park ](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Near South Side ](https://www.expedia.ca/Near-South-Side-Chicago-Hotels-Beach-Hotel.0-n6132399-0-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Near South Side ](https://www.expedia.ca/Near-South-Side-Chicago-Hotels-Cheap-Hotels.0-n6132399-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Free Parking in Near South Side ](https://www.expedia.ca/Near-South-Side-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132399-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Near South Side ](https://www.expedia.ca/Near-South-Side-Chicago-Hotels-Luxury-Hotel.0-n6132399-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Near South Side ](https://www.expedia.ca/Near-South-Side-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132399-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Near South Side Hotels ](https://www.expedia.ca/Near-South-Side-Chicago-Hotels.0-n6132399-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Prairie District ](https://www.expedia.ca/Prairie-District-Chicago-Hotels-Cheap-Hotels.0-n553248635976473159-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Prairie District Hotels ](https://www.expedia.ca/Prairie-District-Chicago-Hotels.0-n553248635976473159-0.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Printers Row ](https://www.expedia.ca/Printers-Row-Chicago-Hotels-Boutique-Hotel.0-n6130106-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Honeymoon Resorts and in Printers Row ](https://www.expedia.ca/Printers-Row-Chicago-Hotels-Honeymoon-Hotels.0-n6130106-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Early Check-in in Printers Row ](https://www.expedia.ca/Printers-Row-Chicago-Hotels-Hotel-With-Early-Check-In.0-n6130106-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Printers Row ](https://www.expedia.ca/Printers-Row-Chicago-Hotels-Luxury-Hotel.0-n6130106-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Ski Hotels in Printers Row ](https://www.expedia.ca/Printers-Row-Chicago-Hotels-Ski-Hotel.0-n6130106-0-tSkiHotel.Travel-Guide-Filter-Hotels)
- [Printers Row Hotels ](https://www.expedia.ca/Printers-Row-Chicago-Hotels.0-n6130106-0.Travel-Guide-Filter-Hotels)
- [Hotels near Roosevelt Station ](https://www.expedia.ca/Roosevelt-Station-Hotels.d6210882.Travel-Guide-Hotels)
- [Resorts in Roosevelt Station ](https://www.expedia.ca/Roosevelt-Station-Resort-Hotels.d6210882-aaResortHotels.Travel-Guide-Accommodation)
- [Villas in Roosevelt Station ](https://www.expedia.ca/Roosevelt-Station-Villas.d6210882-aaVillas.Travel-Guide-Accommodation)
- [Hotels near Soldier Field ](https://www.expedia.ca/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels)
- [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels)
- [Hotels near Wintrust Arena ](https://www.expedia.ca/Wintrust-Arena-Hotels.0-l553248634328853320-0.Travel-Guide-Filter-Hotels)

- [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
- [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

- [900 North Michigan Shops ](https://www.expedia.ca/900-North-Michigan-Shops-Downtown-Chicago.d6199347.Vacation-Attraction)
- [Ann and Robert H. Lurie Children's Hospital ](https://www.expedia.ca/Ann-And-Robert-H-Lurie-Childrens-Hospital-Downtown-Chicago.d553248624898453771.Vacation-Attraction)
- [Aon Center ](https://www.expedia.ca/Aon-Center-Downtown-Chicago.d6064015.Vacation-Attraction)
- [Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
- [Buckingham Fountain ](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction)
- [Cibc Theatre ](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction)
- [Carbide and Carbon Building ](https://www.expedia.ca/Carbide-And-Carbon-Building-Downtown-Chicago.d553248621555594910.Vacation-Attraction)
- [Central Chicago Vacations ](https://www.expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides)
- [Visit Downtown Chicago ](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699)
- [Chicago Harbor Lighthouse ](https://www.expedia.ca/Chicago-Harbor-Lighthouse-Chicago.d6064039.Vacation-Attraction)
- [Visit Near South Side ](https://www.expedia.ca/Chicago-Near-South-Side.dx6132399)
- [Visit Prairie District ](https://www.expedia.ca/Chicago-Prairie-District.dx553248635976473159)
- [Chicago Riverwalk ](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction)
- [Visit The Loop ](https://www.expedia.ca/Chicago-The-Loop.dx800024)
- [Chicago Theatre ](https://www.expedia.ca/Chicago-Theatre-Downtown-Chicago.d6064049.Vacation-Attraction)
- [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides)
- [Cloud Gate ](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction)
- [Downtown Chicago Vacations ](https://www.expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides)
- [Grant Park ](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)
- [House of Blues Chicago ](https://www.expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-Attraction)
- [John Hancock Center ](https://www.expedia.ca/John-Hancock-Center-Downtown-Chicago.d6065131.Vacation-Attraction)
- [Magnificent Mile Vacations ](https://www.expedia.ca/Magnificent-Mile.d800025.Destination-Travel-Guides)
- [Marina City ](https://www.expedia.ca/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction)
- [Michigan Avenue ](https://www.expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)
- [Millennium Park ](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
- [Navy Pier ](https://www.expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)
- [Richard J. Daley Center ](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction)
- [Shops at North Bridge ](https://www.expedia.ca/Shops-At-North-Bridge-Downtown-Chicago.d6227764.Vacation-Attraction)
- [The East Bank Club ](https://www.expedia.ca/The-East-Bank-Club-Downtown-Chicago.d553248621555594881.Vacation-Attraction)
- [The Loop Vacations ](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides)
- [United Center ](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
- [Water Tower Place ](https://www.expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)
- [Willis Tower ](https://www.expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Wrigley Building ](https://www.expedia.ca/Wrigley-Building-Downtown-Chicago.d6064091.Vacation-Attraction)

- [Budget Rental Cars in Central Station ](https://www.expedia.ca/Budget-Car-Rentals-In-Central-Station.d6132250-c39.Car-Rental-Guide-Suppliers)
- [Car rentals near Chicago ](https://www.expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)

- [Things to do in Chicago ](https://www.expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)

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