Memorial Day weekend getaways from Chicago
A long weekend away from Chicago for Memorial Day: fares for Friday, May 28 to Monday, May 31, 2027.
Saved round trips for Memorial Day weekend 2027 (May 28 – May 31, 2027).
Cheapest right now: New York $290 · Denver $298 · Saint George $329
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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 | |
|---|---|---|---|---|
| Myrtle Beach (MYR) | The Grand Strand's beaches and oceanfront boardwalk as the summer season gets going | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
| Panama City (ECP) | Panama City Beach's white sand and the 30A beach towns like Seaside and Rosemary Beach | $964 (airline $1,018) | May 28–31, 2027 | Check prices |
| Fort Walton Beach (VPS) | Destin's emerald water, Crab Island sandbar days and the beaches of Okaloosa Island | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
| Charleston (CHS) | Folly Beach and Isle of Palms, plus dinner in Charleston's historic downtown | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
| Wilmington (ILM) | Wrightsville Beach and Carolina Beach, a short drive from Wilmington's riverwalk | $534 (airline $563) | May 28–31, 2027 | Check prices |
| Norfolk (ORF) | Virginia Beach's oceanfront boardwalk and wide beaches, about half an hour from Norfolk | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
| Portland (PWM) | Portland's Old Port, lobster shacks and Portland Head Light in Cape Elizabeth | $486 (airline $513) | May 28–31, 2027 | Check prices |
| San Diego (SAN) | Coronado's beach, La Jolla Cove's sea lions and the Mission Beach boardwalk | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
| Washington (DCA) | The National Memorial Day Parade on Constitution Avenue and PBS's concert on Sunday night | $335 (airline $353) | May 28–31, 2027 | Check prices |
| New York (JFK) | Rockaway and Coney Island beaches, rooftop bars and the High Line at the unofficial start of summer | $290 (airline $307) | May 28–31, 2027 | Check prices |
| Indianapolis (IND) | The Indianapolis 500 at the Motor Speedway on Sunday, May 30 | No matching fare saved | May 28 – May 31, 2027 (suggested) | Search these dates |
| Nashville (BNA) | Lower Broadway's honky-tonks, a show at the Ryman and East Nashville's patios | $367 (airline $387) | May 28–31, 2027 | Check prices |
| Denver (DEN) | Rocky Mountain National Park, where Trail Ridge Road traditionally opens this weekend | $298 (airline $315) | May 28–31, 2027 | Check prices |
| Bozeman (BZN) | Yellowstone's North Entrance at Gardiner, about 90 minutes south, and Big Sky's trails | $556 (airline $587) | May 28–31, 2027 | Check prices |
| Jackson (JAC) | Grand Teton's peaks and lakes by the airport, with Yellowstone's south gate about an hour north | $4,573 (airline $4,821) | May 28–31, 2027 | Check prices |
| Flagstaff (FLG) | The Grand Canyon's South Rim to the north and Sedona's red rocks to the south | $690 (airline $726) | May 28–31, 2027 | Check prices |
| Saint George (SGU) | Zion National Park, about an hour from St. George, before the summer heat peaks | $329 (airline $348) | May 28–31, 2027 | Check prices |
| Anchorage (ANC) | More than 18 hours of daylight, Turnagain Arm drives and Kenai Fjords cruises from Seward | $536 (airline $566) | May 28–31, 2027 | Check prices |
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
Indy 500 tickets are sold separately. Mountain roads such as Trail Ridge Road open when the snow allows, so check park conditions before you go.
Facts checked October 7, 2026. Sources: OPM: 2027 federal holidays · FOX59: 2027 Indy 500 on May 30, 2027 · PBS: National Memorial Day Concert, May 30, 2027 · American Veterans Center: National Memorial Day Parade · NPS: Trail Ridge Road historically opens Memorial Day weekend
Keep exploring
Hotels in Myrtle Beach with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Myrtle Beach has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
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