Chicago Illinois USA
Big city energy with neighborhood soul.
Chicago rewards anyone willing to explore beyond the skyline.
Top 5 Experiences
Kayaking the Chicago River between downtown skyscrapers
Exploring food stalls at Time Out Market Chicago
Live jazz at Green Mill Cocktail Lounge
Walking the murals of Pilsen
Sunset views from Promontory Point on Lake Michigan
Our Partners
While O’Hare is the most common way to travel to / from Chicago, Amtrak runs an extensive route network to Chicagoland suburbs, regional cities, and long-distance trips. Vakairos celebrates trips with multiple stops and taking more time to enjoy the view
Southwest Airlines
More than 50+ cities fly to Chicago Midway with Southwest! Vakairos customers receive special welcome in Chicago.
Turo
Save time and $ from mega-chain car rental companies and use Turo to rent a car/van with flexible dates, mileage, and pickup/dropoff
Allegiant Airlines
Allegiant operates routes to Chicago Midway, as well as Rockford and Peoria airports at a far more affordable rate. These smaller airports are great for visiting nearby cities like Milwaukee, Quad Cities, or St. Louis.
Partner Spotlight
Lyft
Rideshare options within Chicago are the best option for quick transportation. Save $ and time if you plan to visit multiple spots within walking distance
