Parkside Holidays
Book a Hotel + Flight or Car together to unlock savings
Your Parkside Holiday
Book a custom holiday package to Parkside and prepare to experience this city on your own terms. Think about spending some time in the neighbourhood of Flossmoor, which is good for golfing and lots more. A trip to Parkside is an excellent opportunity to take in the sights. Be sure to stop by big-name attractions such as Hollywood Casino Amphitheatre, Odyssey Fun World and George Dunne National Golf Club. Expedia can help you escape the everyday. Tailor your holiday to Parkside to suit your style of travel, whatever that may look like.
The Latest Parkside Holiday Packages
- Hotel Felix River North/Magnificent Mile
Jul 30 - Aug 4Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights8.2/10 - Very good (2,782 reviews)"Gray stay, centrally located"Reviewed June 10, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 30 - Aug 4Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (2,537 reviews)"The views were beautiful, but the staff was no help. The line was ridiculously long to get checked in. When we got checked in, they had someone show us how to get to our room and the young gentleman brought us to a stairwell and stated didn’t they tell you the elevators are broken we literally had to walk through construction sites and multi levels just to get to our room. I wrote a complaint to the hotel and got little response. The room was beautiful, but poor customer service to say the..."Reviewed June 10, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop - The Emily Hotel
Aug 26 - Sep 1The Emily Hotel + Flight
Downtown Chicago6 nights9.2/10 - Wonderful (1,327 reviews)"Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful. Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the..."Reviewed June 8, 2026Return • London (LHR) - Chicago (ORD)LHR - ORD • 1 stop ORD - LHR • 1 stop£1,791£1,319found 1 day agoper traveller - LondonHouse Chicago, Curio Collection by Hilton
Jul 30 - Aug 4LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (3,731 reviews)"Great breakfast"Reviewed June 10, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop£1,881£1,392found 18 hours agoper traveller - Omni Chicago Hotel
Jul 30 - Aug 4Omni Chicago Hotel + Flight
Downtown Chicago5 nights9.2/10 - Wonderful (1,801 reviews)"Old hotel and rooms. All the outlets in our room were titled and so hard to plug things in them. The outlets near the nightstands on either sides can’t accommodate a charger because they’re stuck on the side of the nightstand between it and the side of the bed. Hairdryer so old and didn’t work. Check in was exactly at 4, they weren’t lenient when I showed up at 2:40."Reviewed June 10, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • 1 stop ORD - DUB • 1 stop£1,847£1,404found 18 hours agoper traveller
Where to stay in Parkside
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.
Top hotels in Parkside
Holiday Inn Chicago – Midway Airport S by IHG
"Bad experience, I recommend to visit this hotel again ever"
Reviewed on 10 Jun 2026
Chicago Club Inn & Suites
"We had two rooms, in one room the sheets were dirty and the air didn’t work. In the other room the air was lukewarm. We were finally given two new rooms , after staying for 3 days we had to ask for towels each day and for the trash to be emptied."
Reviewed on 11 Jun 2026
Sleep Inn Midway Airport Bedford Park
"Hotel"
Reviewed on 10 Jun 2026
Frequently asked questions
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Wendella's 90-min Chicago River Architecture Tour
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.