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Far Southeast Side Cheap Vacations

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*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Cheap vacation packages in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • 1 stop
    CA $952
    CA $710
    per traveller
    found 1 day ago
    Le Méridien Essex Chicago
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,012 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,944
    CA $1,379
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,881 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • 1 stop
    CA $1,108
    CA $795
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Dec 29 - Jan 3

    Park Hyatt Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    "This place was amazing and the hotel staff was extremely helpful"
    Reviewed November 10, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • Nonstop
    CA $3,257
    CA $2,340
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • Dec 19 - Dec 23

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,353
    CA $1,010
    per traveller
    found 2 days ago
    Pendry Chicago

Discover the most popular places to visit in Far Southeast Side

Top Cheap Far Southeast Side Hotels

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.

Frequently Asked Questions

How much does a Far Southeast Side vacation package cost?

We make it easy to see the world, with Far Southeast Side vacation packages starting from as low as CA $710. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate getaway, why not add a couple of tours and activities to your itinerary?

How do I get a cheap travel package to Far Southeast Side?

Combine your hotel and flight bookings, add extras such as a rental car or activities, and save with a Far Southeast Side vacation package. You won't just enjoy impressive discounts on your getaway — you'll have loads of choice at your fingertips too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 properties throughout the world. Your next grand adventure begins right here, right now!

What are the top hotels in Far Southeast Side?

When it comes to properties in Chatham Fields, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are two terrific options. If you're heading to Cheltenham, The Whitehall Hotel and Hyatt Regency Chicago will make you feel right at home.

How far in advance should I book my Far Southeast Side vacation?

It's hard to pick the perfect time for airfares, but we normally say the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you're booking late, don't worry. Cheap prices appear from time to time just weeks before departure dates.

What does an Expedia Far Southeast Side travel package include?

It comes down to what type of trip you have in the works. Far Southeast Side vacation deals can include car rentals, hotels and flights. You can mix and match to create the bundle that suits your needs. You can also add on experiences and activities after you've booked to pick up even bigger discounts.

What should I know before booking a Far Southeast Side travel package?

Bundling your bookings into a Far Southeast Side vacation package is the most convenient 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 tour or an activity?

Can I choose my airline with a Far Southeast Side Expedia vacation package?

Most definitely. Expedia has more than 550 airline partners to choose from worldwide. With such a big range of choice, finding the perfect carrier to whisk you off to Far Southeast Side won't be hard.

If I'm not able to travel, can I cancel my Far Southeast Side vacation package?

You can. We get that even the best-laid plans can fail, so we're happy to help if you have to make changes to your Far Southeast Side vacation package. It may be possible to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.