Search Deals onMagnificent Mile Vacation Packages
Magnificent Mile Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago
Save 100% on your flight
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Woodfield Mall are located nearby.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury 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 Chicago Riverwalk and Millennium Park are located nearby.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 13
found 1 day 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.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 31
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.
Four Points by Sheraton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Fashion Outlets of Chicago are located nearby.
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 31
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.
3-4 Night Vacations in Magnificent Mile
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Magnificent Mile
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Magnificent Mile
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Save an average of 15% on thousands of hotels when you're signed in
Chicago Marriott Downtown Magnificent Mile
540 North Michigan Avenue, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, 4 beach bars, and a rooftop terrace. Our guests praise the bar and the helpful staff ...
Park Hyatt Chicago
800 N Michigan Ave, Chicago, IL
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 in our reviews. ...
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
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 ...
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
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 ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Oct 17 - Mon, Oct 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, just found
$140
Roundtrip
just found
Tue, Jul 15 - Sat, Jul 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 14 hours ago
$255
Roundtrip
found 14 hours ago
Wed, Aug 27 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$555 Roundtrip, found 4 days ago
$555
Roundtrip
found 4 days ago
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$966 Roundtrip, found 5 hours ago
$966
Roundtrip
found 5 hours ago