Title: Near East Side Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $806 Expedia.ca

[Hotels in Near East Side](https://expedia.ca/Near-East-Side-Chicago-Hotels.0-n553248633938968461-0.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)[Near East Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-East-Side.d553248633938968461.Car-Rental-Guide)

![](https://images.trvl-media.com/place/829/cff3ecb3-ae0d-44d6-a966-1057e0d77e80.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Near East Side Vacation Packages

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

Photo by Deano

- ##  
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## Top Holiday Package Deals in Near East Side

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

![Wind Creek Southland Casino and Hotel](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/1fba48a9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Wind Creek Southland Casino and Hotel

East Hazel Crest

CA $806

per person

Apr 23 - Apr 28

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (MDW)

9.4/10 Exceptional! (160 reviews)

Yes, and friendly staff

Reviewed on Feb 27, 2026

![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Banque Hotel

CA $852

per person

Apr 23 - Apr 28

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.4/10 Exceptional! (447 reviews)

Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,286

per person

May 14 - May 18

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 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

CA $1,218

per person

Apr 22 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Great breakfast and friendly staff

Reviewed on Feb 28, 2026

![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 $1,478

per person

Apr 23 - Apr 26

found 18 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at

Reviewed on Feb 26, 2026

## Where to stay in Near East Side

Find the best Near East Side areas and neighborhoods for the activities you enjoy most. [Learn more about Near East Side](https://expedia.ca/Chicago-Near-East-Side.dx553248633938968461)

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

### 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 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://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.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://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(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)

![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.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)

![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(38 area reviews)

 Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. 

[Find hotel + flight trips in O'Hare](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=O%27Hare&DestID=553248635074842747&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Near East Side Hotel Deals

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Swissotel - Chicago

323 E Wacker Dr Chicago IL

Fully refundableReserve now, pay when you stay

CA $166

CA $243 total

Mar 29 - Mar 30

includes taxes & fees

9/10 Wonderful! (3,199 reviews)

Great location

Reviewed on Feb 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=17288&PinnedHotelID=17288&HadPinnedHotel=true&regionId=553248633938968461)

![Radisson Blu Aqua Hotel Chicago](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Radisson Blu Aqua Hotel Chicago

221 N Columbus Dr Chicago IL

Fully refundable

CA $239

CA $316 total

Mar 29 - Mar 30

includes taxes & fees

8.6/10 Excellent! (1,861 reviews)

The was ok until last night that they didn’t clean the room

Reviewed on Feb 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=4520626&PinnedHotelID=4520626&HadPinnedHotel=true&regionId=553248633938968461)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $132

CA $155 total

Mar 2 - Mar 3

includes taxes & fees

8/10 Very Good! (9,895 reviews)

We mainly go to Chicago for medical appointments and it is \*so awesome\* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on Feb 27, 2026

[](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=553248633938968461)

[See all 4,685 properties in Near East Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&regionId=553248633938968461)

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 Near East Side vacation package cost?

### How do I get a cheap travel package to Near East Side?

### Where should I stay in Near East Side?

### What are the top hotels in Near East Side?

### How far in advance should I book my Near East Side vacation?

### What does an Expedia Near East Side travel package include?

### What should I know before booking a Near East Side travel package?

### Can I choose my airline with a Near East Side Expedia vacation package?

### If I'm not able to travel, can I cancel my Near East Side vacation package?

### Discover the most popular places to visit in Near East Side

![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

4.5/5(158 reviews)

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

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-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

4.5/5(19 reviews)

You can enjoy some retail therapy 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.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### Things to do

![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

CA $55

per adult

**94%** of travellers recommend

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

![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)

![cruise ship sailing past navy pier in chicago](https://mediaim.expedia.com/localexpert/173241/21d8d1a0-e61c-4298-ab2f-118c1794b450.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### City Cruises Chicago: Lake Michigan Premier Dinner Cruise

CA $225

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.activity-details)

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=553248633938968461)

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