Title: Cheap Vacations in Central Chicago 2026 | Expedia.ca

![](https://images.trvl-media.com/place/829/bd91735e-0c7e-4d0c-8152-a9d6fd38ff30.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Central Chicago Cheap Vacations

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Photo by Phil Ostroff

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## Flight and Cheap hotel deals in Central Chicago

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

![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $746

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

It’s amazing historical property

Reviewed on Dec 15, 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 $1,902

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 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 $1,995

per person

Jan 24 - Jan 31

found 24 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 2025

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $993

per person

Jan 24 - Jan 31

found 24 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 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 $1,219

per person

Jan 24 - Jan 31

found 24 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap holidays in Central Chicago

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

![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 $1,543

per person

Mar 14 - Mar 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

![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 $1,902

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 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 $1,995

per person

Jan 24 - Jan 31

found 24 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 2025

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap holidays in Central 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 $724

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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 $971

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 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 $1,150

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 2025

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap holidays in Central Chicago

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

![Hyatt Place Chicago/ Schaumburg](https://images.trvl-media.com/lodging/1000000/90000/82300/82257/df623816_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Chicago/ Schaumburg

CA $469

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (1,000 reviews)

Everything was wonderful except those small square pillows, not sure who's idea that was

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 $1,143

per person

Feb 17 - Feb 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 2025

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $566

per person

Feb 17 - Feb 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

Don't see what you're looking for?

See all available trips from Columbus to Central Chicago

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Cheap Hotels in Central Chicago

![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Warwick Allerton - Chicago

701 North Michigan Avenue Chicago IL

- 5 min walk from Michigan Avenue

Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...

8.4/10 Very Good! (3,004 reviews)

Room was great as always, and so walkable to everything, and amazing views. Love this hotel, Ive stayed here many times, and it always has a special place in my memories of Chicago.

Reviewed on Dec 10, 2025

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

- 11 min walk from Michigan Avenue

Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...

8.8/10 Excellent! (3,498 reviews)

Great location! Nice view, good staff

Reviewed on Dec 17, 2025

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![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! (3,150 reviews)

Loved the location and the room was nice with a view!

Reviewed on Dec 14, 2025

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

[See all 1,494 properties in Central Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976475413)

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.

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## More Vacations Ideas

[Flights to Central Chicago

](https://expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights)[

Central Chicago Hotels

](https://expedia.ca/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)[

Central Chicago Vacation Rentals

](https://expedia.ca/Central-Chicago-Vacation-Rentals.d553248635976475413.Travel-Guide-VacationRentals)[

Central Chicago Car Rentals

](https://expedia.ca/Car-Rentals-In-Central-Chicago.d553248635976475413.Car-Rental-Guide)[

Central Chicago Vacations

](https://expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides)[

Things to do in Central Chicago

](https://expedia.ca/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities)

\* 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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