Search Deals onLakeside Vacation Packages
Lakeside Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip 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.
The French Country Inn Lake Geneva
Save 100% on your flight
per person
Aug 7 - Aug 11
found 7 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3-star hotel in Lake Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Geneva Lake and Lake Geneva Cruise Line are located nearby.
The Royal Sonesta Chicago River North
Save 100% on your flight
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant 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
Aug 17 - Aug 23
found 1 day ago
Roundtrip 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
Aug 17 - Aug 23
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.
The Emily Hotel
Save 100% on your flight
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Omni Chicago Hotel
Save 100% on your flight
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North
Save 100% on your flight
per person
Aug 3 - Aug 8
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Lakeside Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Lakeside 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.
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 17 hours ago
$110
Roundtrip
found 17 hours ago
Thu, Jun 5 - Wed, Jun 11
LAX
Los Angeles Intl.
MDW
Midway Intl.
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
Sat, Jun 7 - Tue, Jun 10
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$529 Roundtrip, found 9 hours ago
$529
Roundtrip
found 9 hours ago
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