Title: Near North Side Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $617 Expedia.ca

[Near North Side Travel Guide](https://expedia.ca/Chicago-Near-North-Side.dx137043)[Hotels in Near North Side](https://expedia.ca/Near-North-Side-Chicago-Hotels.0-n137043-0.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 North Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-North-Side.d137043.Car-Rental-Guide)

![](https://images.trvl-media.com/place/137043/3a3332a2-a8e2-4aa9-b29a-c079a4b37d1d.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Near North Side 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 Near North Side

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

![Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination](https://images.trvl-media.com/lodging/1000000/560000/554500/554417/5a40507c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

CA $617

per person

May 22 - May 25

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (998 reviews)

Beautiful rooms and casino i cant wait to return

Reviewed on Mar 2, 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 $1,036

per person

Jun 20 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer. Buffet breakfast is included and that makes it very good value. Hotel also has a gym/ Not too many amenities in the room though.

Reviewed on Apr 2, 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

CA $1,132

per person

Jun 20 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

This hotel provides the basics no amenities you have to pay extra for breakfast and any amenities you would like.

Reviewed on Apr 3, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,340

per person

May 23 - May 26

found 16 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

Great location and property

Reviewed on Mar 14, 2026

![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Le Méridien Essex Chicago

Downtown Chicago

CA $1,111

per person

Jun 19 - Jun 22

found 15 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

8.8/10 Excellent! (1,012 reviews)

Bar was well-stocked, shops nearby are great

Reviewed on Mar 29, 2026

## Where to stay in Near North Side

Find the best Near North Side areas and neighborhoods for the activities you enjoy most. [Learn more about Near North Side](https://expedia.ca/Chicago-Near-North-Side.dx137043)

![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 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](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](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(733 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)

![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(39 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)

![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

 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)

## Near North Side Hotel Deals

![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

CA $180

CA $211 total

Apr 5 - Apr 6

includes taxes & fees

9/10 Wonderful! (4,042 reviews)

No free WiFi. $70 for overnight parking. They do have a breakfast restaurant on the lobby floor

Reviewed on Apr 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=137043)

![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

CA $199

CA $233 total

Apr 12 - Apr 13

includes taxes & fees

8.6/10 Excellent! (5,811 reviews)

Great property; great location!

Reviewed on Apr 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=137043)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $170

CA $239 total

Apr 5 - Apr 6

includes taxes & fees

9.4/10 Exceptional! (3,712 reviews)

The breakfast was very good. They had a great selection of food

Reviewed on Apr 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true&regionId=137043)

[See all 1,016 properties in Near North Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&regionId=137043)

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 North Side vacation package cost?

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

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

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

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

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

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

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

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

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

![Water Tower Place](https://images.trvl-media.com/place/6064087/b6a04578-7f57-4437-b0b1-672d4ae44f19.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

[](https://expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)

![875 North Michigan Avenue](https://images.trvl-media.com/place/6065131/31560e8f-121e-4823-9cdb-02b104f564cc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 875 North Michigan Avenue

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums. 

[](https://expedia.ca/875-North-Michigan-Avenue-Downtown-Chicago.d6065131.Vacation-Attraction)

![Chicago skyline at twilight.](https://images.trvl-media.com/place/6227753/83a45f2c-01e6-4a04-ad16-c633333fadc2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### House of Blues Chicago

You can get tickets for a performance at House of Blues Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area. 

[](https://expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-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

CA $37

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.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

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

**94%** of travellers recommend

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

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=137043)

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