Fair Plain Flight + Hotel Packages

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

Holiday Inn Express Chicago-Downers Grove by IHG

Save 100% on your flight

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Book a stay at this business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yorktown Shopping Center and Morton Arboretum are located nearby.

Fairmont Chicago at Millennium Park

Save 100% on your flight

per person

May 20 - May 23

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, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Spark by Hilton Stevensville

Save 100% on your flight

per person

May 22 - May 27

found 19 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Book a stay at this business-friendly hotel in Stevensville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Silver Beach and Grand Mere State Park are located nearby.

Embassy Suites by Hilton Chicago Downtown River North

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Glen Club

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per person

Jun 12 - Jun 16

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Stay at this 3.5-star golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and Kohl Children's Museum are located nearby.

Wrigleyville Suites

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per person

May 29 - Jun 1

found 16 hours ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

Stay at this aparthotel in Chicago. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.

The Boulevard Inn & Bistro

Save 100% on your flight

per person

May 22 - May 27

found 19 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Stay at this 3.5-star hotel in Saint Joseph. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Silver Beach and FuzzyButz Pet Bakery are located nearby.

The Chicago Hotel Collection River North

Save 100% on your flight

per person

Jul 3 - Jul 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Stay at this 3-star hotel in Chicago. Enjoy free WiFi, a fitness center, and 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.

Fair Plain Vacation Packages 3-4 Night Stays

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

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Save 100% on your flight

per person

Jul 3 - Jul 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Save 100% on your flight

per person

Jul 3 - Jul 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)