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Eagle Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
per person
Jul 19 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Jul 19 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.

Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

La Banque Hotel
Save 100% on your flight
per person
Jul 3 - Jul 6
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.

DayDreamer Domes
Save 100% on your flight
per person
Jul 13 - Jul 19
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star hotel in South Haven. Enjoy free parking, room service, and onsite spa services. Popular attractions Kal Haven Trail and Michigan Maritime Museum are located nearby.

Radisson Blu Aqua Hotel Chicago
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Victoria Resort and Bed & Breakfast
per person
Jul 13 - Jul 19
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Kal Haven Trail are located nearby.

Congress Plaza Hotel
per person
Jul 19 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Eagle Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Eagle Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Thu, May 29 - Sun, Jun 1
LAX
Los Angeles Intl.
MKE
General Mitchell Intl.
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago

Sat, Jun 14 - Wed, Jun 18
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$143 Roundtrip, found 5 days ago
$143
Roundtrip
found 5 days ago

Tue, Jul 1 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago

Mon, Jul 28 - Fri, Aug 1
DEN
Denver Intl.
MKE
General Mitchell Intl.
$168 Roundtrip, found 5 hours ago
$168
Roundtrip
found 5 hours ago
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