Southern Wisconsin Packages (Flight + Hotel)

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Top Southern Wisconsin Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ฿95,219, price is now ฿61,706 per person
฿61,706
per person
26 Jul - 2 Aug
found 4 hours ago
Return direct flight included
Barranquilla (BAQ) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.

Reviewed on 23 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ฿135,488, price is now ฿84,990 per person
฿84,990
per person
26 Jul - 2 Aug
found 5 hours ago
Return direct flight included
Barranquilla (BAQ) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Excelente, ubicación perfecta cerca de todo

Reviewed on 23 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ฿144,855, price is now ฿95,382 per person
฿95,382
per person
26 Jul - 2 Aug
found 5 hours ago
Return direct flight included
Barranquilla (BAQ) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.

Reviewed on 24 Jun 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ฿105,432, price is now ฿70,377 per person
฿70,377
per person
26 Jul - 2 Aug
found 5 hours ago
Return direct flight included
Barranquilla (BAQ) to Chicago (ORD)
9/10 Wonderful! (1,023 reviews)
Perfect location! Room immaculate! Vibes perfect! Staff amazing & extremely helpful & accommodating!

Reviewed on 26 Jun 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ฿122,903, price is now ฿83,960 per person
฿83,960
per person
26 Jul - 2 Aug
found 5 hours ago
Return direct flight included
Barranquilla (BAQ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The hotel is beautiful with so many bars and restaurants nearby. About 4 -5 blocks from Millenium Park. The seating areas are so peaceful and the design is amazing. They let me store my bike box the day before my stay which was so convenient. Staff are friendly and professional.

Reviewed on 17 Jun 2026

Where to stay in Southern Wisconsin

Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern Wisconsin
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Cathedral Square are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Top hotels in Southern Wisconsin

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
The price is ฿3,502 per night from 16 Jul to 17 Jul
฿3,502
฿3,931 total
16 Jul - 17 Jul
includes taxes & fees
7/10 Good! (2,834 reviews)
"The room was clean and nice. Beds were very creaky every time you moved. Check in was a bit difficult with language issues with the workers but went fairly smooth. Walls and doors were not soundproof at all. You could hear the other guests all night like they were in you room. Getting to Waterpark ..."

Reviewed on 25 Jun 2026

Mt. Olympus Water & Theme Park Resort
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is ฿3,941 per night from 5 Jul to 6 Jul
฿3,941
฿4,553 total
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (3,892 reviews)
"Great location in Madison."

Reviewed on 24 Jun 2026

The Madison Concourse Hotel and Governor's Club
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is ฿5,254 per night from 30 Jun to 1 Jul
฿5,254
฿6,195 total
30 Jun - 1 Jul
includes taxes & fees
9.2/10 Wonderful! (1,571 reviews)
"I have stayed in two different rooms. One completely smelled like smoke. One was very, very clean. The staff is very friendly and helpful. The check-in process is extremely quick. The Asian restaurant by the elevator is absolutely incredible. The service at the rock ‘n’ roll bar especially one bartender ..."

Reviewed on 26 Jun 2026

Potawatomi Hotel & Casino
See all 7,608 properties in Southern Wisconsin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Southern Wisconsin attractions

Slidewheel water at a water park.

Mt. Olympus Water and Theme Park

7.4/5 (1,284 reviews)
Have a fun-filled day at Mt. Olympus Water and Theme Park and see why people love this theme park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.
See properties

Frequently asked questions

Can I cancel my flight booking to Southern Wisconsin due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for almost every travel question, including about flight changes related to COVID-19. For more peace of mind, we recommend looking over the terms and conditions of your airfare before booking a seat.
What's the best way to find cheap flights to Southern Wisconsin that have flexible change policies?
By using our clever "No change fee" filter, that's how. All you have to do is enter your preferred dates and destination, click "Search," then click the checkbox directly under the "Flexible change policies" heading (it's on the left of your screen). Expedia makes it a snap to find inexpensive, flexible tickets to Southern Wisconsin.
What are some of the general tips for travellers to Southern Wisconsin during the COVID-19 outbreak?
In the face of the COVID-19 outbreak, travelling now comes with some extra challenges. Make a note of these valuable tips before jumping on your flight to Southern Wisconsin:
  • Understand what, if any, restrictions or rules apply to both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book your flight.
  • Wear a face mask during airport screening. A TSA employee will ask you to temporarily lower your mask for ID purposes.
  • Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. After that, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
  • Put any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection.

Which airlines fly to Southern Wisconsin?
Delta offers flights into or near Southern Wisconsin, including 573 that arrive at General Mitchell Intl. Airport (MKE) each month. Figure out your travel dates and then book your fare early for the best deal.
How can I find cheap tickets to Southern Wisconsin?
Book ahead of time, fly to or from nearby airports, avoid school holiday time — there are lots of ways! Another one is to take advantage of Expedia's "flexible dates" function. Search for your Southern Wisconsin flight, then check out the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to Southern Wisconsin was .
How much is a flight to Southern Wisconsin?
One-way flights leaving () sold for as low as in the last seven days. During this period, the cost of a round-trip journey to Southern Wisconsin ranged between and . If you find a fantastic deal, book fast — these prices don't wait around for long.
What are the most popular airports to fly into in Southern Wisconsin?
Get ready to pack your bags and fly into General Mitchell Intl. Airport (MKE), Southern Wisconsin's leading flight hub. Book one of the 2400 flights that touch down at this popular destination each month.
When is the cheapest time to fly to Southern Wisconsin?
Leave for Southern Wisconsin early on in the week and you'll usually be rewarded with cheaper fares. Tuesday is known for being the cheapest day to get on a plane, closely followed by Monday. If you're hoping to avoid the costliest flights, stay away from Saturdays.
How much is a plane ticket to Southern Wisconsin?
In the last seven days, airfares to Southern Wisconsin ranged between and . Prices depend on multiple things, particularly the departure time, airline, seating class and when you make your booking.
Which airlines with flights to Southern Wisconsin employ COVID-19 cleanliness policies?
As lockdowns and restrictions start to lift, airlines are back in the skies with new strategies including physical distancing and an increased supply of face masks, gloves and sanitizer. Here's what some carriers are doing to help stop the spread of COVID-19:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.