Oakton Vacations
Book a Hotel + Flight or Car together to unlock savings
Your Oakton Vacation
Book a customized Oakton vacation package that has everything you need and nothing you don't. Good for cafes, nature and bars and pubs, consider staying in the neighborhood of Rogers Park. There's loads to see and do during your trip to Oakton, including Rivers Casino and Arndt Park. Expedia has what you need to escape your daily routine. Tailor your vacation to Oakton to suit your style of travel, whatever that may be.
- Swissotel - Chicago
Aug 4 - Aug 8Swissotel - Chicago + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (3,358 reviews)"Staff was so helpful"Reviewed May 29, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Aug 4 - Aug 8Hotel Riu Plaza Chicago + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (4,297 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Aug 19 - Aug 23Level 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 • Boston (BOS) - Chicago (MDW)BOS - MDW • Nonstop MDW - BOS • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Aug 4 - Aug 8Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (2,513 reviews)"Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes."Reviewed May 28, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - LondonHouse Chicago, Curio Collection by Hilton
Aug 4 - Aug 8LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (3,723 reviews)"Great experience"Reviewed May 30, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
Where to stay in Oakton
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.
Oakton Hotel Deals
Congress Plaza Hotel
"Great location and clean"
Reviewed on May 29, 2026
Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile
"Asked for a room with a tub didn't get it and got extra charges after stay. Got my full deposit back but got extra charges. And paid for breakfast after being told it was included. No cable on tv"
Reviewed on May 30, 2026
Discover the most popular places to visit in Oakton
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
