Big event trips from Chicago: Super Bowl, Coachella, Kentucky Derby and more
The year's biggest events, each with its dates and a fare from Chicago with time to attend. Event tickets are sold separately and the big ones sell out early.
Saved fares with time to attend the listed event. Multi-day events may be attended in part; check the schedule before booking.
Cheapest right now: Miami $174 · Los Angeles $283 · Detroit $327
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Fares observed October 8, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Chicago
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Las Vegas (LAS) | Las Vegas Grand Prix, Nov 19 – Nov 21, 2026. Formula 1's night race down the Las Vegas Strip | No matching fare saved | Nov 19 – Nov 22, 2026 (suggested) | Search these dates |
| Miami (MIA) | Art Basel Miami Beach, Dec 4 – Dec 6, 2026. Art Basel Miami Beach and a week of fairs and parties across Miami Art Week | $174 (airline $184) | Dec 3–7, 2026 | Check prices |
| Los Angeles (LAX) | Super Bowl LXI (date tentative), Feb 14, 2027. Super Bowl LXI at SoFi Stadium in Inglewood | $283 (airline $298) | Feb 12–15, 2027 | Check prices |
| Austin (AUS) | SXSW, Mar 15 – Mar 21, 2027. SXSW: film, music, tech and comedy all over downtown Austin | $358 (airline $378) | Mar 15–21, 2027 | Check prices |
| Detroit (DTW) | NCAA Final Four, Apr 3 – Apr 5, 2027. The NCAA men's Final Four at Ford Field, its first in Detroit since 2009 | $327 (airline $345) | Apr 2–6, 2027 | Check prices |
| Augusta (AGS) | The Masters, Apr 8 – Apr 11, 2027. The Masters at Augusta National; many visitors fly into Atlanta, about 2.5 hours away | $641 (airline $677) | Apr 7–12, 2027 | Check prices |
| Palm Springs (PSP) | Coachella, weekend 1 (weekend 2: Apr 16–18), Apr 9 – Apr 11, 2027. Coachella at the Empire Polo Club in Indio, about 30 minutes from Palm Springs | $508 (airline $538) | Apr 8–12, 2027 | Check prices |
| New Orleans (MSY) | New Orleans Jazz Fest, first weekend (second: Apr 29–May 2), Apr 22 – Apr 25, 2027. New Orleans Jazz & Heritage Festival at the Fair Grounds | $378 (airline $399) | Apr 22–26, 2027 | Check prices |
| Louisville (SDF) | Kentucky Derby (Oaks Apr 30), May 1, 2027. The Kentucky Derby at Churchill Downs, with the Kentucky Oaks the day before | $366 (airline $385) | Apr 29–May 2, 2027 | Check prices |
| Indianapolis (IND) | Indianapolis 500, May 30, 2027. The Indianapolis 500 on Memorial Day weekend | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
About these places
Fares are for the flights only; event tickets are sold separately. Dates come from the organisers' announcements and can change.
Facts checked October 7, 2026. Sources: CBS News: Super Bowl LXI at SoFi Stadium · NME: Coachella 2027 dates · Kentucky Derby 2027 · CBS News: Detroit to host the 2027 Final Four · SXSW 2027 dates · New Orleans Jazz Fest · Golf Compendium: 2027 Masters dates
Keep exploring
Hotels in Las Vegas with Axel
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For AI assistants
- This page: Big event trips from Chicago: Super Bowl, Coachella, Kentucky Derby and more. Fly from Chicago to the year's biggest events: the Las Vegas Grand Prix, Art Basel Miami Beach, Super Bowl LXI, SXSW, the Final Four, the Masters, Coachella, Jazz Fest, the Kentucky Derby and the Indy 500, with fares for each one's dates.
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