Jeffrey Manor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • Indoor wedding
    Jul 1 - Jul 4

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,352 reviews)
    "Clean. Comvienent"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $996
    CA $707
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Smart TV
    Aug 2 - Aug 8

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,919
    CA $1,699
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Full-size fridge, microwave, oven, stovetop
    Aug 2 - Aug 8

    Level Chicago – Old Town + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.0/10 - Wonderful (481 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,741
    CA $1,702
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • View from property
    Jul 1 - Jul 4

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (117 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,162
    CA $787
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Lounge
    Jun 30 - Jul 3

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,121 reviews)
    "The staff were extremely accommodating and friendly."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,162
    CA $842
    per traveller
    found 1 day ago
    Pendry Chicago

Where to stay in Jeffrey Manor

Find the best Jeffrey Manor areas and neighborhoods for the activities you enjoy most. Learn more about Jeffrey Manor
Downtown Chicago

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 hotels in Downtown Chicago

Jeffrey Manor Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is CA $187 per night from May 27 to May 28
CA $187
CA $222 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (10,144 reviews)
"Our hvac unit in the room was one of the loudest I’ve ever had the displeasure of sleeping near. Had to turn it off to get sleep. Great views but definitely some historic wear that needs new paint in halls, elevator entries, etc. front doors were partially defunct our entire stay. No onsite parking ..."

Reviewed on May 26, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is CA $248 per night from May 27 to May 28
CA $248
CA $334 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,255 reviews)
"Excellent staff and breakfast. Great location and beatiful view from floor 27 rooftop."

Reviewed on May 26, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is CA $263 per night from Jun 3 to Jun 4
CA $263
CA $312 total
Jun 3 - Jun 4
includes taxes & fees
7.8/10 Good! (1,478 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on May 26, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,226 properties in Jeffrey Manor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Jeffrey Manor vacation package cost?
Our Jeffrey Manor packages, which start at just , are an easy way to save. Choose your favorite hotels, flights and more to create your perfect trip.
How do I get a cheap travel package to Jeffrey Manor?
If you love amazing deals, combine your bookings into a Jeffrey Manor vacation package. Whether you're looking for hotels, flights, activities or rental cars, you can book everything in one place. You'll have lots of choice at your fingertips as well. Expedia has more than 550 partner airlines and 1,000,000 properties around the globe to choose from. Fly with who you want, find a room where you like and save a packet — now that's the ideal escape!
Where should I stay in Jeffrey Manor?
With fascinating attractions such as Calumet Beach and Calumet Park in this neighborhood, look for a hotel positioned near them. Harborside International Golf Center is another sight that visitors flock to.
How far in advance should I book my Jeffrey Manor vacation?
It can be difficult to know exactly when the best time is to book your Jeffrey Manor vacation. But typically the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels up to 12 months prior to your departure date. If you're thinking of a last-minute getaway, no need to stress! There are terrific deals announced on Expedia all the time.
What does an Expedia Jeffrey Manor travel package include?
That depends on you. You can pick from a range of Jeffrey Manor packages, such as a flight, rental car and hotel. You can also book a flight and a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your dream Jeffrey Manor trip looks like, you'll save!
What should I know before booking a Jeffrey Manor travel package?
Bundling your bookings into a Jeffrey Manor vacation package is the easiest way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Jeffrey Manor Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to select from around the globe. With so many choices, finding the ideal carrier to bring you to Jeffrey Manor will be a breeze.
If I'm not able to travel, can I cancel my Jeffrey Manor vacation package?
If your vacation plans in Jeffrey Manor have been upended, it's good to know that you can amend or cancel your booking. If you made your booking in the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Jeffrey Manor

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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

Michigan Avenue

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.

Michigan Avenue

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.