Cheap Vacations in Wisconsin

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Wisconsin vacations

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
The Loop
Price was $994, price is now $777 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop

4 out of 5
The Loop
Price was $823, price is now $686 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Hotel Monaco Chicago, an IHG Hotel

Kimpton Hotel Monaco Chicago, an IHG Hotel

4.5 out of 5
Theatre District
Price was $714, price is now $608 per person
per person
Jul 2 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
The Loop
Price was $826, price is now $708 per person
per person
Jul 2 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Hotel Lincoln, part of JdV by Hyatt

Hotel Lincoln, part of JdV by Hyatt

4 out of 5
Old Town Triangle
Price was $571, price is now $492 per person
per person
Jun 21 - Jun 24
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
The Loop
Price was $699, price is now $604 per person
per person
Jul 2 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
River North
Price was $797, price is now $689 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
River North
Price was $671, price is now $580 per person
per person
Jul 2 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
River North
Price was $699, price is now $606 per person
per person
Jul 2 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
The Westin Chicago River North

The Westin Chicago River North

4.5 out of 5
River North
Price was $900, price is now $782 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)

3-night Wisconsin vacations

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flightPrice was $1,598, price is now $1,243 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Price was $994, price is now $777 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
Price was $839, price is now $671 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Hotel Monaco Chicago, an IHG Hotel

Kimpton Hotel Monaco Chicago, an IHG Hotel

4.5 out of 5
Price was $834, price is now $674 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Price was $820, price is now $664 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
Price was $939, price is now $765 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $886, price is now $736 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Thompson Chicago

Thompson Chicago

4.5 out of 5
Price was $785, price is now $653 per person
per person
Jul 1 - Jul 4
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop

4 out of 5
Price was $823, price is now $686 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Price was $829, price is now $696 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Drake

The Drake

4 out of 5
Price was $731, price is now $618 per person
per person
Jun 21 - Jun 24
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Selina Chicago

Selina Chicago

3.5 out of 5
Price was $720, price is now $610 per person
per person
Jun 24 - Jun 27
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

4-night Wisconsin vacations

Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Save 100% on your flightPrice was $1,053, price is now $794 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flightPrice was $2,041, price is now $1,550 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Kimpton Hotel Monaco Chicago, an IHG Hotel

Kimpton Hotel Monaco Chicago, an IHG Hotel

4.5 out of 5
Price was $1,079, price is now $830 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Price was $863, price is now $678 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $894, price is now $717 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Thompson Chicago

Thompson Chicago

4.5 out of 5
Price was $1,146, price is now $934 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
theWit Chicago - a DoubleTree by Hilton Hotel

theWit Chicago - a DoubleTree by Hilton Hotel

4.5 out of 5
Price was $1,174, price is now $958 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Price was $944, price is now $779 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $959, price is now $796 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Price was $1,124, price is now $936 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
Price was $910, price is now $767 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Price was $865, price is now $731 per person
per person
Jun 23 - Jun 27
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Top places to visit in Wisconsin

Wisconsin Vacation Deal FAQ's

Where to find Wisconsin package deals?

On CheapTickets, you can find package deals in Wisconsin and save up to $287.

When is peak season in Wisconsin?

are very popular times to visit Wisconsin.

When is the best time to visit Wisconsin?

If you're looking for cheap vacations to Wisconsin, is the best time to visit Wisconsin.

When is the worst time time to visit Wisconsin?

Prices for Wisconsin vacations can peak during .

When is low season in Wisconsin?

We have found to be the least-crowded time of the year to visit Wisconsin.

Flight deals to Wisconsin

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 7 - Tue, Sep 13
DEN
Denver
MSP
Minneapolis
$134 Roundtrip, found 9 hours ago
Sun Country Airlines
Thu, May 26 - Sun, May 29
DEN
Denver
GRB
Green Bay
$155 Roundtrip, found 1 days ago
Frontier Airlines
Thu, Sep 15 - Fri, Sep 30
EWR
Newark
MSP
Minneapolis
$170 Roundtrip, found 13 hours ago
Sun Country Airlines
Tue, Aug 30 - Wed, Sep 14
EWR
Newark
MKE
Milwaukee
$173 Roundtrip, found 6 days ago
American Airlines
Thu, Nov 24 - Sun, Dec 4
AZA
Mesa
MSP
Minneapolis
$176 Roundtrip, found 2 days ago
Sun Country Airlines
Tue, Oct 18 - Sat, Oct 22
PHX
Phoenix
MSP
Minneapolis
$176 Roundtrip, found 12 hours ago
Sun Country Airlines

Top rated hotels for your Wisconsin vacation

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI, 53147
155.48 mi from city center
The price is $169 per night
With a stay at Timber Ridge Lodge and Waterpark in Lake Geneva, you'll be in a regional park, within a 10-minute drive of Geneva Lake and Dan Patch Stables.
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI, 53965
Free Cancellation
Reserve now, pay when you stay
70.23 mi from city center
The price is $30 per night
Located in Wisconsin Dells, Mt. Olympus Water & Theme Park Resort is within a 5-minute drive of Ghost Outpost and Top Secret.
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street, Milwaukee, WI, 53233
Free Cancellation
Reserve now, pay when you stay
142.73 mi from city center
The price is $139 per night
When you stay at Potawatomi Hotel & Casino in Milwaukee, you'll be near the airport, within a 5-minute drive of Harley-Davidson Museum and The Rave-Eagles Club.
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.