Southmoor 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.
  • Bar (on property)
    Jul 23 - Jul 27

    The Whitehall Hotel, BW Premier Collection + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    8.4/10 - Very good (3,926 reviews)
    "The staff was so gracious and accommodating and the location was perfect for walking to shopping, restaurants, coffee, everything. The rooms were also spacious and had a comfortable seating area. Would definitely stay here again!"
    Reviewed June 3, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    €1,317
    €1,043
    per traveller
    found 22 hours ago
    The Whitehall Hotel, BW Premier Collection
  • Smart TV
    Jul 23 - Jul 27

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    €1,640
    €1,251
    per traveller
    found 22 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 23 - Jul 27

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,526 reviews)
    "Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission."
    Reviewed June 4, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    €1,636
    €1,299
    per traveller
    found 22 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 23 - Jul 27

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,727 reviews)
    "Great location, excellent room and amenities proactively attentive staff."
    Reviewed June 4, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    €1,590
    €1,268
    per traveller
    found 22 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Lobby
    Jul 23 - Jul 27

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.2/10 - Very good (2,758 reviews)
    "The staff were friendly and helpful."
    Reviewed June 5, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    €1,487
    €1,190
    per traveller
    found 22 hours ago
    Hotel Felix River North/Magnificent Mile

Where to stay in Southmoor

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

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 €140 per night from 29 Jun to 30 Jun
€140
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,179 reviews)
"Location was good to train station and grand park but biggest issue we had is no water pressure and it was at best lukewarm. This makes me now want to always check first before booking anything how their water service is. It was terrible and when I checked previous reviews it was one of biggest complaints. ..."

Reviewed on 6 Jun 2026

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €257 per night from 2 Jul to 3 Jul
€257
2 Jul - 3 Jul
includes taxes & fees
8.6/10 Excellent! (2,476 reviews)
"Check in was horrible. The longest lines you can imagine….face me 250 Hilton points….not useful for me. Property is beautiful if you look closely but it is not well maintained."

Reviewed on 4 Jun 2026

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
The price is €162 per night from 1 Jul to 2 Jul
€162
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (2,239 reviews)
"I had an amazing time in Chicago, not one complaint. Everyone was pleasant and my room was clean."

Reviewed on 4 Jun 2026

Crowne Plaza Chicago West Loop by IHG
See all 2,467 properties in Southmoor
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 Southmoor holiday package cost?
Less than you might think — from as low as , as a matter of fact! By combining hotels, flights and car rentals into a custom-made package, your getaway to Southmoor is just a few clicks away.
How do I get a cheap travel package to Southmoor?
Our Southmoor holiday packages promise plenty of savings for the savvy globetrotter. For the best deals, simply bundle your hotel, flights and tours into an affordable package. But low prices are just the beginning of your next awesome adventure. When you book with Expedia, you'll have more than 550 airlines and 1,000,000 hotels across the globe to pick from. Whatever your budget or style, there's a holiday package with your name on it.
Where should I stay in Southmoor?
With fascinating attractions such as Orland Square and Centennial Park Aquatic Centre in this neighbourhood, look for a hotel situated near them. University Of Chicago Medicine is another sight in Southmoor that draws the crowds.
How far in advance should I book my Southmoor holiday?
You'll be rewarded with the biggest variety at the lowest prices by booking your holiday to Southmoor nice and early. Air carriers generally sell flight tickets anywhere up to a year in advance, so secure your spot ASAP. Having said that, Expedia is dedicated to giving you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Southmoor travel package include?
Travel packages include rental cars, hotels and flights, but you can mix and match them to create your dream Southmoor trip. You can also add on fun stuff like tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Southmoor travel package?
You'll score big savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one spot just makes things easier. So why waste your time or money? Whether you're organising a fancy romantic getaway or a low-cost family break, explore our package deals today.
Can I choose my airline with a Southmoor Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just choose the carrier that suits you and put together your ideal Southmoor holiday.
If I'm not able to travel, can I cancel my Southmoor holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Southmoor holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Popular places to visit

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
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€36
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.