Chicago Flight + Hotel Packages

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Staybridge Suites Chicago O'Hare - Rosemont by IHG

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per person

Aug 3 - Aug 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.

Trump International Hotel & Tower Chicago

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per person

Aug 3 - Aug 8

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.

Palmer House a Hilton Hotel

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per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. 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.

Hotel Felix River North/Magnificent Mile

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per person

Jul 18 - Jul 21

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.

Kimpton Gray Hotel by IHG

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per person

Aug 7 - Aug 11

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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

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per person

Aug 3 - Aug 8

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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Hilton Chicago/Magnificent Mile Suites

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per person

Jul 18 - Jul 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Radisson Blu Aqua Hotel Chicago

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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.

Chicago Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.