Title: Honeymoon Vacations in Chicago 2026 | Expedia.ca

![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chicago Honeymoon Vacations

## 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

## Flight and Honeymoon hotel deals in Chicago

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

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $591

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

7.6/10 Good! (1,001 reviews)

Clean room, good service and great area.

Reviewed on Dec 18, 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 $1,017

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,787 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,254

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

CA $751

per person

Feb 22 - Feb 27

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (3,392 reviews)

Great service. Thoughtful management sent us chocolates for our anniversary. Beautiful rooms, daily room refresh, awesome rooftop and views. Helpful staff. Loved everything.

Reviewed on Dec 19, 2025

![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Omni Chicago Hotel

Downtown Chicago

CA $979

per person

Mar 15 - Mar 19

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,603 reviews)

Perfect location in the heart of the Magnificent Mile. Great holiday ambiance

Reviewed on Dec 17, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Honeymoon holidays in Chicago

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

![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 $1,017

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,787 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,254

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,129

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

It is always an amazing place to stay

Reviewed on Nov 26, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Honeymoon holidays in Chicago

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

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $591

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

7.6/10 Good! (1,001 reviews)

Clean room, good service and great area.

Reviewed on Dec 18, 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 $1,141

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,787 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,254

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Honeymoon holidays in Chicago

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

![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 $896

per person

Feb 11 - Feb 15

found 8 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Excellent location to stay in the heart of the city.

Reviewed on Dec 17, 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 $1,409

per person

Feb 11 - Feb 15

found 8 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,787 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,762

per person

Feb 11 - Feb 15

found 8 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Honeymoon Hotels in Chicago

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Eurostars Magnificent Mile

660 North State Street Chicago IL

- 5 min walk from Michigan Avenue

Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...

8.8/10 Excellent! (3,149 reviews)

The staff were great. However, the room shook whenever someone closed a door to another room in the hall. This made it hard to get a good sleep. Their choice of toilet tissue was surprisingly cheap. Single ply TP is something you use if there’s no other option, not in a decent hotel in a major city ...

Reviewed on Dec 19, 2025

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Wade

644 N Lake Shore Dr Chicago IL

- 7 min walk from Michigan Avenue

Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...

8.4/10 Very Good! (1,521 reviews)

Yes

Reviewed on Dec 15, 2025

[](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Hyatt Lodge Oak Brook Chicago](https://images.trvl-media.com/lodging/1000000/50000/49500/49450/13282144_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Lodge Oak Brook Chicago

2815 Jorie Blvd Oak Brook IL

- 29 min drive from Michigan Avenue

Book a stay at this spa hotel in Oak Brook. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...

8.8/10 Excellent! (1,002 reviews)

nice clean room

Reviewed on Dec 9, 2025

[](https://expedia.ca/Chicago-Hotels-Hyatt-Lodge.h49450.Hotel-Information)

[See all 5,618 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=178248)

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.

## More vacations you might like

![](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)

## More Vacations Ideas

[Flights to Chicago

](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[

Chicago Hotels

](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[

Chicago Vacation Rentals

](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[

Chicago Car Rentals

](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[

Chicago Vacations

](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)[

Things to do in Chicago

](https://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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app