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TravelPirates
Profile
Flights
Vacation
Hotels
Airbnb
Cruises
Others
Last-Minute
All-Inclusive
Solo Travel
January
February
National Holidays
Beach Vacations
LGBTQ+ Travel
Family Vacation
USA
Caribbean
Mexico
Europe
Asia
From NYC
From LA
From Chicago
From South Florida
From Bay Area
From Texas
From DC
From Boston
From Canada
TravelPirates

Hand-picked deals by our pirate team

Get inspired!

Hand-picked deals by our pirate team
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Check Out Our Most Recent Deals to the Midwest
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Hotels
🤯 This BrewDog Hotel Has a Draft Tap In Every Room 🍻
From $104 per Night with Free Welcome Beer and Breakfast Included 😎
From $104
Vacations
Affordable Chicago Getaway with Luxe Thompson Hotel 🛎️✨
3-Night Chicago Vacation from $321—Includes Airfare & Thompson by Hyatt Hotel
From $321
Vacations
3-Nights to Discover Chicago's Vibe in the $200s w/ Flights
Don't Just Visit Chicago, Live it from $270 - Windy City Getaway with Jazz, Art, and Adventure 🎷🖼️💃🍕
From $270
Vacations
⛸ Skate On Over to Chicago for a Spectacular Weekend Vacay!
Save upwards of 20% on these 3-Star weekend getaways to the Windy City this fall and winter - flights and up to 3-night hotel stay included!
From $255
Vacations
✈️ 3 Night CLEVELAND, Ohio Escape from mid 200s! 🏙️
🤩 3 Nights Top Rated B&B + RT Flights to Cleveland, Ohio from $267 per person! 🇺🇸
From $267
Vacations
🦡Give It The Old College Try With These Madison Weekends!
Head off to beautiful Wisconsin for a weekend on the lake, college football and Halloween! Flights and hotel stays included in these great vacays!
From $350
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The Midwest: 12 States in the North-Central Part of the US

Discover the best discounts and offers for exploring the heart of America. Whether you're planning a weekend getaway to the Great Lakes, a scenic road trip through rolling farmlands, or an adventure in vibrant cities like Chicago, Minneapolis, or St. Louis, we’ve got you covered. Our curated travel deals will help you experience the Midwest's hidden gems, outdoor wonders, and rich cultural history without breaking the bank. Start planning your next Midwest adventure with unbeatable savings today!

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