Summer is a great time to be in Chicago with a multitude of options for tourists and locals alike. There’s shopping along Michigan Avenue; museums for adults and children of every age; fireworks not once, but twice a week all summer long at Navy Pier; concerts in Grant Park and Millennium Park, with most of them being free; panoramic views of the city and Lake Michigan from the top of the John Hancock Tower and the Sears…I mean, Willis Tower; winning and losing professional sports teams; and more dining options than you can shake a stick at.
If you want to hang with the locals, there’s a neighborhood festival almost every weekend through the end of September, with food vendors from local restaurants and musical performances — check the City of Chicago’s Web site for a complete list of festivals. And if you get too hot and/or need a break from the city, you can head over to one of the many beaches along Lake Michigan and cool down by taking a dip. If you need more convincing on why you should visit Chicago, check out our recent blog post that highlights summer activities in Chicago for all tastes. Or if you already know you want to visit the Windy City, then hurry and grab one of these low fares our experts have found!
Cheap Flights to Chicago
These fares are not part of an airline sale and may disappear at any time, so book ASAP!
Availability varies by route. Click on the Fare Calendar Links below to find the best dates to travel to Chicago through October, unless otherwise noted (all prices roundtrip, including taxes):
- $72-$90 — Minneapolis
- $88-$138 — Denver Travel Sept.-Dec.
- $108-$138 — Boston Travel Sept.-Oct. 5
- $174 — St. Louis Travel Sept.-Dec.
- $214 — New York City Travel Nov.-Feb.
- $236 — San Diego
- More cheap flights to Chicago
After booking the fare of your choice, make sure to consult Travelzoo’s Chicago Destination page for savings of up to 50% off hotel, entertainment, and attraction deals.
Other Flight Deals
Our experts have uncovered several other amazing deals this week, domestic and international. Here is a compilation of our favorites.
Travel September to December, unless otherwise noted. Click on the Fly.com Fare Calendar links below to find the best dates to travel (all prices roundtrip, including taxes):
- $118 — Atlanta to Orlando
- $118 — Phoenix to Los Angeles
- $138 — San Francisco to San Diego Travel Aug.-Oct.
- $375 — Denver to Hamilton, Bermuda
- $382-$395 — Detroit to San Juan, Puerto Rico
- $509 — New York City to Dublin, Ireland Travel Nov., Jan. & Feb.
- $539-$569 — Boston to Dublin, Ireland Travel Nov., Jan. & Feb.
- $644-$652 — Washington, D.C. to Tel Aviv, Israel Travel Nov., Jan. & Feb.
- $806 — Washington, D.C. to Johannesburg, South Africa Travel Nov., Jan. & Feb.
- $851 — Washington, D.C. to Dubai, UAE Travel Nov., Jan. & Feb.
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- Low Fare Calendars – This tool shows the best deals from the nearest major airport and allows users to create a custom fare calendar for any route (scroll to the bottom for this functionality).