50 destinations. Each price uses the nights and dates shown, with a private room, daily spending and a 10% planning allowance.
Totals are for one traveller. Prices updated 1 min ago. Fetch time is separate from when each fare was found.
4–7 nights, with 7 preferred when prices are close. Ranked by whole-trip cost per night.
Mexico · Latin America
Mexico's cultural capital — birthplace of tequila, mariachi, and the iconic torta ahogada.
5 nights · Sun 8 Nov–Fri 13 Nov
About $825
Total for one
$165 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Mexico · Latin America
Massive capital with world-class museums, ancient Aztec ruins, incredible tacos, and vibrant neighborhoods.
7 nights · Tue 22 Dec–Tue 29 Dec
About $1,310
Total for one
$187 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Poland · Eastern Europe
Medieval charm with Europe's largest market square, Wawel Castle, and a legendary nightlife district.
7 nights · Tue 1 Dec–Tue 8 Dec
About $1,316
Total for one
$188 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Vietnam · Southeast Asia
Charming Old Quarter, steaming pho stalls, and French colonial architecture on the banks of Hoan Kiem Lake.
7 nights · Tue 10 Nov–Tue 17 Nov
About $1,550
Total for one
$221 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Peru · Latin America
South America's culinary capital with ceviche, Pisco sours, and pre-Inca ruins.
7 nights · Tue 24 Nov–Tue 1 Dec
About $1,648
Total for one
$235 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Mexico · Latin America
Caribbean turquoise waters, Mayan ruins at Tulum and Chichén Itzá, and all-inclusive resort paradise.
7 nights · Fri 13 Nov–Fri 20 Nov
About $1,653
Total for one
$236 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Venice of America with yacht-filled canals, Fort Lauderdale Beach, and a launching point for the Bahamas.
7 nights · Thu 29 Oct–Thu 5 Nov
About $1,660
Total for one
$237 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Mile High City with craft breweries, Rocky Mountain National Park access, and a thriving arts district.
7 nights · Mon 9 Nov–Mon 16 Nov
About $1,666
Total for one
$238 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Southern capital with the Martin Luther King Jr. historic site, BeltLine trails, and a world-class food scene.
5 nights · Thu 12 Nov–Tue 17 Nov
About $1,206
Total for one
$241 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Metroplex hub with the JFK memorial, Fort Worth stockyards, and Texas-sized BBQ and Tex-Mex culture.
7 nights · Thu 5 Nov–Thu 12 Nov
About $1,699
Total for one
$243 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Egypt · Africa
Pyramids of Giza, the Egyptian Museum, Khan el-Khalili bazaar, and 5,000 years of civilization on the Nile.
7 nights · Sun 1 Nov–Sun 8 Nov
About $1,729
Total for one
$247 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Mauritius · Africa
Volcanic island paradise with turquoise lagoons, rum distilleries, Creole cuisine, and giant tortoises.
4 nights · Thu 26 Nov–Mon 30 Nov
About $2,870
Total for one
$718 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Japan · East Asia
Neon-lit megacity blending ancient temples with cutting-edge technology, ramen, and cherry blossoms.
7 nights · Sat 21 Nov–Sat 28 Nov
About $2,680
Total for one
$383 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
South Korea · East Asia
K-pop, kimchi, ancient palaces, neon-lit streets, and some of the best street food in Asia.
6 nights · Mon 30 Nov–Sun 6 Dec
About $2,561
Total for one
$427 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Bulgaria · Eastern Europe
Underrated capital with Ottoman mosques, Soviet monuments, and hip cafés at Eastern European prices.
7 nights · Sun 1 Nov–Sun 8 Nov
About $1,754
Total for one
$251 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Poland · Eastern Europe
Renaissance Old Market Square with mechanical goats on the clock tower, croissant museums, and student energy.
5 nights · Thu 26 Nov–Tue 1 Dec
About $1,411
Total for one
$282 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Colombia · Latin America
Walled colonial city on the Caribbean with colourful balconies, salsa rhythms, and the Rosario Islands offshore.
5 nights · Mon 14 Dec–Sat 19 Dec
About $1,218
Total for one
$244 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Dominican Republic · Latin America
All-inclusive Caribbean paradise with palm-fringed beaches, golf courses, and Saona Island day trips.
5 nights · Mon 9 Nov–Sat 14 Nov
About $1,279
Total for one
$256 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Jamaica · Latin America
Jamaica's resort coast with jerk-chicken shacks, Dunn's River Falls, reggae beats, and Blue Mountain coffee.
5 nights · Mon 9 Nov–Sat 14 Nov
About $1,553
Total for one
$311 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Turkey · Middle East
Where East meets West — Byzantine mosaics, Ottoman mosques, rooftop terraces, and the Grand Bazaar.
6 nights · Fri 30 Oct–Thu 5 Nov
About $1,872
Total for one
$312 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Turkey · Middle East
Turquoise Coast resort city with Kaleiçi old town, Düden waterfalls, and ancient Aspendos theatre.
6 nights · Sun 8 Nov–Sat 14 Nov
About $1,897
Total for one
$316 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
UAE · Middle East
Superlative city of the world's tallest building, luxury malls, desert safaris, and beach clubs.
7 nights · Tue 3 Nov–Tue 10 Nov
About $2,785
Total for one
$398 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Qatar · Middle East
Futuristic skyline, the Museum of Islamic Art, desert excursions, and World Cup legacy venues.
7 nights · Tue 3 Nov–Tue 10 Nov
About $3,007
Total for one
$430 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Music City — honky-tonk bars on Broadway, the Ryman Auditorium, and hot chicken that will change your life.
6 nights · Tue 24 Nov–Mon 30 Nov
About $1,531
Total for one
$255 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Birthplace of America — Independence Hall, cheesesteaks, Rocky’s steps, and a thriving arts district.
7 nights · Sun 27 Dec–Sun 3 Jan
About $1,843
Total for one
$263 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Neon-lit Strip, world-class shows, desert hikes at Red Rock Canyon, and the Hoover Dam nearby.
4 nights · Sun 15 Nov–Thu 19 Nov
About $1,055
Total for one
$264 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Research Triangle hub with a thriving food hall scene, outdoor concert venues, and easy mountain escapes.
6 nights · Tue 29 Dec–Mon 4 Jan
About $1,608
Total for one
$268 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Canada · North America
Fortress city with cobblestone streets, the Château Frontenac, and the best poutine in French Canada.
7 nights · Thu 10 Dec–Thu 17 Dec
About $1,897
Total for one
$271 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
America’s Finest City with Balboa Park, La Jolla coves, Mexican border culture, and perfect weather.
5 nights · Thu 5 Nov–Tue 10 Nov
About $1,423
Total for one
$285 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Desert metropolis with Camelback Mountain hikes, cowboy heritage, and resort pools under endless sunshine.
4 nights · Sun 22 Nov–Thu 26 Nov
About $1,156
Total for one
$289 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
The Big Easy — French Quarter jazz, Creole cuisine, voodoo history, and nonstop festival energy.
4 nights · Thu 19 Nov–Mon 23 Nov
About $1,192
Total for one
$298 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Alamo city with River Walk margaritas, missions history, and the best breakfast tacos in Texas.
4 nights · Fri 30 Oct–Tue 3 Nov
About $1,237
Total for one
$309 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Pike Place Market, grunge history, craft coffee roasters, tech-campus energy, and the Olympic Mountains nearby.
7 nights · Mon 16 Nov–Mon 23 Nov
About $2,501
Total for one
$357 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Beach culture, Hollywood glamour, taco trucks, and year-round California sunshine.
7 nights · Thu 5 Nov–Thu 12 Nov
About $2,691
Total for one
$384 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Canada · North America
Canada’s capital with Parliament Hill, the Rideau Canal, and a surprisingly strong culinary renaissance.
4 nights · Fri 30 Oct–Tue 3 Nov
About $1,584
Total for one
$396 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Freedom Trail, Harvard and MIT, Red Sox at Fenway, New England seafood, and autumn foliage day trips.
4 nights · Thu 26 Nov–Mon 30 Nov
About $1,600
Total for one
$400 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Waikiki Beach, Diamond Head crater, Pearl Harbor history, and Polynesian culture on O'ahu.
7 nights · Sun 15 Nov–Sun 22 Nov
About $2,841
Total for one
$406 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
Smithsonian museums (free!), the National Mall, cherry blossoms, and Georgetown's townhouse charm.
4 nights · Fri 30 Oct–Tue 3 Nov
About $1,657
Total for one
$414 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Canada · North America
Mountain-meets-ocean city with Stanley Park, Granville Island, ski slopes, and Pacific Rim cuisine.
5 nights · Thu 12 Nov–Tue 17 Nov
About $2,107
Total for one
$421 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United States · North America
The city that never sleeps — Broadway, Central Park, world cuisine, and iconic skyline.
5 nights · Thu 26 Nov–Tue 1 Dec
About $2,202
Total for one
$440 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Estonia · Northern Europe
Medieval Old Town meets digital innovation — Estonia's gem with cobblestones and craft beer.
7 nights · Mon 9 Nov–Mon 16 Nov
About $2,164
Total for one
$309 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
United Kingdom · Northern Europe
Royal palaces, West End theater, world-class museums (free!), and a global food scene.
7 nights · Tue 1 Dec–Tue 8 Dec
About $3,053
Total for one
$436 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Maldives · South Asia
Overwater villas, bioluminescent beaches, world-class diving, and barefoot luxury in the Indian Ocean.
6 nights · Thu 29 Oct–Wed 4 Nov
About $3,842
Total for one
$640 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Greece · Southern Europe
Ancient Acropolis overlooking a modern city with street art, rooftop tavernas, and island ferries on your doorstep.
6 nights · Wed 18 Nov–Tue 24 Nov
About $1,744
Total for one
$291 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Italy · Southern Europe
Fashion capital with Da Vinci's Last Supper, the Duomo, and aperitivo culture at its finest.
7 nights · Mon 30 Nov–Mon 7 Dec
About $2,410
Total for one
$344 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Spain · Southern Europe
World-class art museums, grand plazas, late-night tapas culture, and the beating heart of Spain.
4 nights · Fri 30 Oct–Tue 3 Nov
About $1,624
Total for one
$406 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Portugal · Southern Europe
Pastel-colored hills, vintage trams, world-class pastéis de nata, and a thriving creative scene.
4 nights · Sat 7 Nov–Wed 11 Nov
About $1,640
Total for one
$410 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Italy · Southern Europe
Eternal City of Colosseum, Vatican, fountains, and the best pasta and gelato on the planet.
4 nights · Thu 19 Nov–Mon 23 Nov
About $1,872
Total for one
$468 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Austria · Western Europe
Imperial palaces, coffee house culture, classical music, and the best Sachertorte in the world.
7 nights · Mon 7 Dec–Mon 14 Dec
About $2,322
Total for one
$332 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
France · Western Europe
The City of Light — Eiffel Tower, Louvre, café terraces, and patisseries on every corner.
4 nights · Thu 29 Oct–Mon 2 Nov
About $2,209
Total for one
$552 per night · whole trip
Recent fare
Local transport is in daily spending. Airport transfers are extra.
Enter your budget and dates to discover destinations within reach of Chicago. These page-level fare estimates are a starting point — always confirm the final price before booking.