Near South Side Vacations
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Your Near South Side Vacation
Lock in a vacation package to Near South Side and immerse yourself in everything this lakeside neighborhood has to offer. Noted for its history, walking and culture, your next exciting adventure can be found right here. Start your trip to Near South Side by checking out nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help turn your ideal Near South Side vacation into reality, no matter your travel plans or budget.
- The Royal Sonesta Chicago River North
Jul 8 - Jul 11The Royal Sonesta Chicago River North + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (2,616 reviews)"Loved the hotel and staff"Reviewed May 29, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - Level Chicago Fulton Market
Jul 10 - Jul 14Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (490 reviews)"Amazing place"Reviewed May 26, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - Hotel Riu Plaza Chicago
Jul 8 - Jul 11Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (4,292 reviews)"We did find some small issues with the cleanliness of the room. Great location. Beautiful hotel. Amazing rooftop bar experience. We had a great stay."Reviewed May 30, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop - Urban Chicago Oasis
Jul 23 - Jul 27Urban Chicago Oasis + Flight
Lakeview4 nightsRoundtrip • New York (LGA) - Chicago (MDW)LGA - MDW • Nonstop ORD - JFK • Nonstop - Level Chicago – Old Town
Jul 10 - Jul 14Level Chicago – Old Town + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (484 reviews)"Staff was amazing and the apartment building was phenomenally clean!"Reviewed May 28, 2026Roundtrip • Atlanta (ATL) - Chicago (MDW)ATL - MDW • Nonstop MDW - ATL • Nonstop
Where to stay in Near South Side
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.
Near South Side Hotel Deals
Hyatt Regency McCormick Place Chicago
"I loved how nice the room was"
Reviewed on May 30, 2026
Congress Plaza Hotel
"Great location and clean"
Reviewed on May 29, 2026
Hotel Riu Plaza Chicago
"We did find some small issues with the cleanliness of the room. Great location. Beautiful hotel. Amazing rooftop bar experience. We had a great stay."
Reviewed on May 30, 2026
Discover the most popular places to visit in Near South Side
Lakefront Trail
Lakefront Trail is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Wander the lakeside and beautiful beaches in the area.
Burnham Park
After visiting Burnham Park, make a plan to see the other sights and activities in Chicago. Stroll along the area's lakeside, or simply savor its top-notch restaurants.
Things to do
