The best US cities to visit from Chicago
City trips from Chicago to the best places to visit in the US, each with what to see and the cheapest round trip we've seen recently.
The cheapest matching round trip we’ve seen recently for each destination.
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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 | |
|---|---|---|---|---|
| New York (JFK) | Central Park, Broadway, the Met and the High Line, plus Brooklyn's food and bars | No matching fare saved | Search other dates | |
| Boston (BOS) | The Freedom Trail, Fenway Park and the North End's Italian bakeries | No matching fare saved | Search other dates | |
| Washington (DCA) | The Smithsonian's free museums on the National Mall and the monuments lit up at night | No matching fare saved | Search other dates | |
| Philadelphia (PHL) | The Liberty Bell and Independence Hall, Reading Terminal Market and a cheesesteak | No matching fare saved | Search other dates | |
| New Orleans (MSY) | The French Quarter, live jazz on Frenchmen Street and Creole cooking in the Garden District | No matching fare saved | Search other dates | |
| Nashville (BNA) | Broadway's honky-tonks, the Ryman Auditorium and the Country Music Hall of Fame | No matching fare saved | Search other dates | |
| San Francisco (SFO) | The Golden Gate Bridge, Alcatraz, cable cars and dim sum in Chinatown | No matching fare saved | Search other dates | |
| Seattle (SEA) | Pike Place Market, the Space Needle and ferry rides across Puget Sound | No matching fare saved | Search other dates | |
| Austin (AUS) | Live music on Sixth Street and South Congress, Texas barbecue and Barton Springs | No matching fare saved | Search other dates | |
| San Diego (SAN) | Balboa Park, the Gaslamp Quarter and La Jolla's sea lions, in mild weather all year | No matching fare saved | Search other dates | |
| Charleston (CHS) | Charleston's Battery, Rainbow Row and Lowcountry cooking in the historic district | No matching fare saved | Search other dates | |
| Savannah (SAV) | Savannah's historic squares under live oaks and the cobblestones of River Street | No matching fare saved | Search other dates | |
| Portland (PDX) | Portland's food carts, Powell's City of Books and the Columbia River Gorge nearby | No matching fare saved | Search other dates | |
| Denver (DEN) | Denver's LoDo breweries, Red Rocks Amphitheatre and the Rockies an hour west | No matching fare saved | Search other dates | |
| Miami (MIA) | Miami Beach's Art Deco district, Little Havana's Calle Ocho and Wynwood's murals | No matching fare saved | Search other dates | |
| Los Angeles (LAX) | Hollywood, Griffith Observatory, the Getty and the beach at Santa Monica | No matching fare saved | Search other dates | |
| Las Vegas (LAS) | The Strip's shows and restaurants, with Red Rock Canyon a short drive west | No matching fare saved | Search other dates | |
| Oahu / Honolulu (HNL) | Waikiki, Pearl Harbor's memorials and the hike up Diamond Head | No matching fare saved | Search other dates | |
| Minneapolis (MSP) | Minneapolis' chain of lakes, the Walker Art Center and the Guthrie Theater | No matching fare saved | Search other dates | |
| Pittsburgh (PIT) | Pittsburgh's three rivers, the Andy Warhol Museum and the inclines up Mount Washington | No matching fare saved | Search other dates | |
| Atlanta (ATL) | The Martin Luther King Jr. National Historical Park, the Georgia Aquarium and the BeltLine | No matching fare saved | Search other dates | |
| San Antonio (SAT) | The River Walk, the Alamo and the old Spanish missions along the San Antonio River | No matching fare saved | Search other dates | |
| Santa Fe (SAF) | Santa Fe's adobe Plaza, Canyon Road's galleries and the Georgia O'Keeffe Museum | No matching fare saved | Search other dates |
About these places
Facts checked October 7, 2026. Sources: Smithsonian Institution (Wikipedia): free admission · Saint Louis Zoo: visit
Keep exploring
Hotels in New York with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in New York has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: The best US cities to visit from Chicago. The best US cities to visit from Chicago: New York, Chicago, Boston, Washington DC, New Orleans, Nashville, San Francisco, Austin and more, with real round-trip fares.
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