South Shore Holidays

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  • Better together

    Save up to €900 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.
  • Lobby
    Jul 3 - Jul 7

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.2/10 - Very good (2,747 reviews)
    Return • New York (JFK) - Chicago (ORD)
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    Save 100% on your flight
    €674
    €453
    per traveller
    found 6 hours ago
    Hotel Felix River North/Magnificent Mile
  • Smart TV
    Jul 3 - Jul 7

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (492 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • New York (JFK) - Chicago (ORD)
    JFK - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    €864
    €593
    per traveller
    found 6 hours ago
    Level Chicago Fulton Market
  • Indoor wedding
    Jul 3 - Jul 7

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,360 reviews)
    "The gym is on 43 floor.. amazing"
    Reviewed May 31, 2026
    Return • New York (JFK) - Chicago (ORD)
    JFK - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    €771
    €535
    per traveller
    found 6 hours ago
    Swissotel - Chicago
  • Breakfast and dinner served
    Jul 3 - Jul 7

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,787 reviews)
    "Restaurant is excellent. Breakfast is excellent. Doorman & all entrance staff are terrific & helpful. We never received the $25 food coupons as advertised. From Exxpedia??? or from Omni???"
    Reviewed June 2, 2026
    Return • New York (JFK) - Chicago (ORD)
    JFK - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    €670
    €473
    per traveller
    found 6 hours ago
    Omni Chicago Hotel
  • Exterior detail
    Jul 3 - Jul 7

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,318 reviews)
    "Convenient location and easy building to deal with. Parking was a little expensive."
    Reviewed June 2, 2026
    Return • New York (JFK) - Chicago (ORD)
    JFK - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    €899
    €651
    per traveller
    found 6 hours ago
    The Emily Hotel

Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore
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

Top hotels in South Shore

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €143 per night from 29 Jun to 30 Jun
€143
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,159 reviews)
"Hotel was clean, staff friendly. Old hotel that is being improved. Our room was small but otherwise good for our purposes. Good spot that launch our adventure!"

Reviewed on 3 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €155 per night from 28 Jun to 29 Jun
€155
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,506 reviews)
"I did not stay because my medical reason for booking this was canceled. They would not work with me to change the dates."

Reviewed on 2 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €218 per night from 30 Jun to 1 Jul
€218
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,323 reviews)
"Clean room, the breakfast was great, and the lobby bar serves a really good guava lemon drop!"

Reviewed on 3 Jun 2026

Hotel Riu Plaza Chicago
See all 4,435 properties in South Shore
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 South Shore holiday package cost?
Starting from an incredible , you can handcraft your own South Shore package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to South Shore?
Just think of all the awesome things you could do in South Shore with a pile of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a South Shore holiday package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 hotel options globally. Whether you're enjoying a break with the entire family or going it alone, exploring South Shore is better with a package.
Where should I stay in South Shore?
Holiday Makers come from far and wide to experience University of Chicago and Chicago Museum of Science and Industry in South Shore. Stay within walking distance of these fantastic attractions and visit them whenever you please.
How far in advance should I book my South Shore holiday?
Search Expedia to compare international fares as soon as possible. You can usually purchase a seat up to 12 months before departure. If you can't see your preferred air carrier, or you have to book last minute, don't despair. Cheap tickets to South Shore sometimes emerge a few weeks before departure.
What does an Expedia South Shore travel package include?
That depends on what you want. If you're travelling solo, you might decide to combine flights and hotels. Bringing the whole family to South Shore? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a South Shore travel package?
You'll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and score fantastic discounts. Hotels aren't your only option, however. We have island resorts, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a South Shore Expedia holiday package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Simply select the carrier you want and put together your ideal South Shore holiday.
If I'm not able to travel, can I cancel my South Shore holiday package?
We understand — sometimes life doesn't go according to plan. If you've booked a South Shore holiday package and have to amend or cancel it, we can help. It's always worth checking out our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Stay near popular South Shore attractions

Rainbow Beach

Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.