Southmoor Vacations
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Your Southmoor Vacation
Prepare to experience Southmoor on your own terms with a custom Southmoor vacation package! Uncovering the best parts of this lively city is made easier with a base in a neighborhood such as Flossmoor, which is good for golfing, among other things. You'll want to do a little exploring during your trip to Southmoor. Don't miss leading attractions such as Orland Park Sportsplex, Orland Square and Centennial Park. A couple of quick clicks is all it takes to put together a tailored Southmoor vacation on Expedia.
- Dorothy's
Jul 23 - Jul 26Dorothy's + Flight
Lakeview3 nights8.6/10 - Excellent (132 reviews)"This was kinda misleading it was more like a hostel without being budget friendly . Unfortunately the people who had rooms next to us was rude enough to drink my soda. Little to say won't be staying in a place like this again. Very noisy at night and unaware a club was under us and went on til 4am. Parking is horrible. Why offer parking if there is no designated parking? Very misleading when I booked this room. They make it like you are staying at a bed and breakfast but not the case. Room is..."Reviewed May 27, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - ATL • Nonstop$698$496found 1 day agoper traveler - Urban Chicago Oasis
Jul 23 - Jul 27Urban Chicago Oasis + Flight
Lakeview4 nightsRoundtrip • New York (LGA) - Chicago (MDW)LGA - MDW • Nonstop ORD - JFK • Nonstop - Swissotel - Chicago
Jul 10 - Jul 13Swissotel - Chicago + Flight
Downtown Chicago3 nights9.0/10 - Wonderful (3,353 reviews)"Is a great little action to downtown places/parks and the river walk."Reviewed May 28, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Trump International Hotel & Tower Chicago
Jul 10 - Jul 13Trump International Hotel & Tower Chicago + Flight
Downtown Chicago3 nights9.6/10 - Exceptional (1,881 reviews)"We had an amazing time, we absolutely loved our stay"Reviewed May 29, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - Pendry Chicago
Jul 23 - Jul 26Pendry Chicago + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (1,122 reviews)"The staff were extremely accommodating and friendly."Reviewed May 25, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - ATL • Nonstop
Where to stay in Southmoor
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Southmoor Hotel Deals
Congress Plaza Hotel
"The Congress is old but it never fails!!! Great location!!! I have stayed there many of times …"
Reviewed on May 28, 2026
Crowne Plaza Chicago West Loop by IHG
"Clean room"
Reviewed on May 29, 2026
Hilton Chicago
"Clean room, updated but no room service and quality restaurant was disappointing"
Reviewed on May 29, 2026
Discover the most popular places to visit in Southmoor
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
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.
Things to do
