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Fri, May 1 - Sun, May 3
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$611 Roundtrip, just found
$611
Roundtrip
just found
Select Delta flight, departing Fri, May 1 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, May 3, priced at $611 just found
Tue, May 12 - Wed, May 13
MSP
Minneapolis
MKE
Milwaukee
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, May 12 from Minneapolis to Milwaukee, returning Wed, May 13, priced at $241 found 2 days ago
Tue, May 12 - Wed, May 13
MSP
Minneapolis
MKE
Milwaukee
$284 Roundtrip, found 2 days ago
$284
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, May 12 from Minneapolis to Milwaukee, returning Wed, May 13, priced at $284 found 2 days ago
Tue, May 12 - Wed, May 13
MSP
Minneapolis
MKE
Milwaukee
$290 Roundtrip, found 2 days ago
$290
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, May 12 from Minneapolis to Milwaukee, returning Wed, May 13, priced at $290 found 2 days ago
Mon, Jun 1 - Fri, Jun 5
MSP
Minneapolis
MKE
Milwaukee
$297 Roundtrip, found 3 days ago
$297
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Jun 1 from Minneapolis to Milwaukee, returning Fri, Jun 5, priced at $297 found 3 days ago
Fri, Jul 24 - Sun, Jul 26
MSP
Minneapolis
MKE
Milwaukee
$299 Roundtrip, found 2 hours ago
$299
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Jul 24 from Minneapolis to Milwaukee, returning Sun, Jul 26, priced at $299 found 2 hours ago
Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

8.8/10 Excellent! (1,006 reviews)

Jun 11 - Jun 14

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Minneapolis (MSP)

Frontier Airlines • Coach
Price was $950, price is now $695 per person
$695
per person
found 1 day ago
I enjoyed my stay here. The location was perfect for walking around. We were able to walk to every attraction on our list . The only thing missing is a pool!

Reviewed on Jul 27, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,458 reviews)

Jun 4 - Jun 8

4 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Minneapolis (MSP)

Sun Country Airlines • Coach
Save 100% on your flight
Price was $1,988, price is now $1,277 per person
$1,277
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,848 reviews)

Jun 4 - Jun 8

4 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Minneapolis (MSP)

Sun Country Airlines • Coach
Save 100% on your flight
Price was $2,063, price is now $1,422 per person
$1,422
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

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Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago - Oak Forest by IHG
2.5-star property

Holiday Inn Express & Suites Chicago - Oak Forest by IHG

8.8/10 Excellent! (553 reviews)

Jun 19 - Jun 21

2 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $892, price is now $826 per person
$826
per person
found 18 hours ago
Very clean rooms and building. Staff is the best. Theo, Bri and Toi are so accomadating

Reviewed on Jan 17, 2026

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5-star property

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

9.6/10 Exceptional! (1,002 reviews)

Jun 19 - Jun 21

2 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,443, price is now $1,302 per person
$1,302
per person
found 18 hours ago
Phenomenal location, so many things within walking distance

Reviewed on May 13, 2025

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5-star property

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

9/10 Wonderful! (1,312 reviews)

Jun 19 - Jun 21

2 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $952, price is now $878 per person
$878
per person
found 18 hours ago
Everything was great. Barbara at the front desk was especially helpful

Reviewed on Jan 12, 2026

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.