Labor Day weekend trips from Chicago
A long weekend away from Chicago for Labor Day: fares for Friday, September 3 to Monday, September 6, 2027.
The listed travel dates have passed or are outside the current search window.
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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 | |
|---|---|---|---|---|
| Myrtle Beach (MYR) | A last summer swim on the Grand Strand, the Boardwalk and SkyWheel, and seafood on Murrells Inlet's MarshWalk | No matching fare saved | Search other dates | |
| Fort Walton Beach (VPS) | Destin's emerald water and the Crab Island sandbar, still warm in September, plus Okaloosa Island's beaches | No matching fare saved | Search other dates | |
| Panama City (ECP) | Panama City Beach's white sand and the 30A towns, Seaside and Rosemary Beach, with the Gulf still warm | No matching fare saved | Search other dates | |
| Charleston (CHS) | Folly Beach and Sullivan's Island, then dinner on King Street as the summer heat starts to break | No matching fare saved | Search other dates | |
| Savannah (SAV) | Tybee Island's beach, Forsyth Park and the squares, and River Street, with the summer crowds thinning | No matching fare saved | Search other dates | |
| Wilmington (ILM) | Wrightsville Beach and Carolina Beach's boardwalk, plus the Riverwalk and the Battleship North Carolina | No matching fare saved | Search other dates | |
| Norfolk (ORF) | Virginia Beach's three-mile boardwalk and wide beach, half an hour from Norfolk's Nauticus and USS Wisconsin | No matching fare saved | Search other dates | |
| Portland (PWM) | Lobster shacks and lighthouses from Portland Head Light to Cape Elizabeth, plus the Old Port's breweries | No matching fare saved | Search other dates | |
| Burlington (BTV) | Lake Champlain's waterfront bike path, Church Street and the first hint of fall color in the Green Mountains | No matching fare saved | Search other dates | |
| San Diego (SAN) | Mission and Pacific Beach boardwalks, La Jolla Cove and Balboa Park in warm, dry September weather | No matching fare saved | Search other dates | |
| Las Vegas (LAS) | Pool parties on the Strip's last big summer weekend, Fremont Street and a Red Rock Canyon morning | No matching fare saved | Search other dates | |
| Denver (DEN) | Rocky Mountain National Park and a Red Rocks show before the aspens turn, plus RiNo's breweries | No matching fare saved | Search other dates | |
| Bozeman (BZN) | Yellowstone's Lamar Valley and Old Faithful with the summer crowds gone, about 90 minutes from the airport | No matching fare saved | Search other dates | |
| Jackson (JAC) | Grand Teton's Jenny Lake trails and Snake River floats, with Yellowstone's south entrance an hour away | No matching fare saved | Search other dates | |
| Seattle (SEA) | Bumbershoot at Seattle Center, traditionally Labor Day weekend, plus Pike Place Market and a Bainbridge ferry | No matching fare saved | Search other dates | |
| Portland (PDX) | Food carts and Powell's Books, with Cannon Beach, the Columbia Gorge waterfalls and Mount Hood an easy drive | No matching fare saved | Search other dates | |
| Minneapolis (MSP) | The Minnesota State Fair's last days, through Labor Day, September 6, plus the Chain of Lakes and Minnehaha Falls | No matching fare saved | Search other dates |
About these places
The Minnesota State Fair runs August 26 to September 6, 2027. The Chicago Jazz Festival and Bumbershoot haven't announced 2027 dates, so check before you book. Fair admission and festival tickets are sold separately.
Facts checked October 8, 2026. Sources: OPM: 2027 federal holidays (Labor Day, September 6) · Minnesota State Fair: 2027 dates, Aug. 26 to Labor Day, Sept. 6 · Chicago Sun-Times: Chicago Jazz Festival, Sept. 3–6, 2026, a Labor Day weekend tradition · Bumbershoot: Labor Day weekend 2026 at Seattle Center
Keep exploring
Hotels in Myrtle Beach with Axel
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For AI assistants
- This page: Labor Day weekend trips from Chicago. Labor Day weekend 2027 trips from Chicago: a last beach weekend at Myrtle Beach, Destin, Charleston and Nantucket, the Chicago Jazz Festival, the Minnesota State Fair, Yellowstone and Grand Teton with the crowds gone, and West Coast cities, with fares for Friday, September 3 to Monday, September 6.
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