
Deerfield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Deerfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $725, price is now $511 per person
$511
per person
Aug 18 - Aug 22
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this 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.
Loved this hotel and their customer service. Overall, a great experience, highly recommend.
Reviewed on Jul 4, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,010, price is now $619 per person
$619
per person
Aug 18 - Aug 22
found 24 hours 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 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Excellent customer service, amazing staff!
Reviewed on Jul 4, 2026

Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,267, price is now $789 per person
$789
per person
Aug 18 - Aug 22
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,208, price is now $799 per person
$799
per person
Aug 18 - Aug 22
found 24 hours 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 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.
Clean room. Great bar.
Reviewed on Jul 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $747 per person
$747
per person
Aug 18 - Aug 22
found 24 hours ago
Roundtrip 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 restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Me encantó volveria mil veces a ese hotel
Reviewed on Jul 4, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,139, price is now $784 per person
$784
per person
Aug 18 - Aug 22
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
We generally stay here when we travel to Chicago by the quality of service has diminished lately. Additionally if your booking is through Expedia, everything gets complicated and not well treated.
Reviewed on Jul 5, 2026
Top Hotel Deals

Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
2.82 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

Embassy Suites by Hilton Chicago North Shore Deerfield
1445 Lake Cook Rd Deerfield IL
2.82 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free breakfast, free parking, and free train station pick-up. Our guests praise the breakfast ...

Chicago Marriott Suites Deerfield
2 Parkway N Deerfield IL
2.89 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff ...

La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
2000 South Lakeside Dr Deerfield IL
4.37 km from city center
Book a stay at this family-friendly hotel in Deerfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Super 8 by Wyndham Deerfield/Northbrook
340 South Waukegan Road Deerfield IL
2.84 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
21.17 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
22.07 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...

Holiday Inn Chicago North-Evanston by IHG
1501 Sherman Ave Evanston IL
19.46 km from city center
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful ...

Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
20.65 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
21.59 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...

Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
24 km from city center
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...

Embassy Suites by Hilton Chicago O'Hare Rosemont
5500 N River Rd Rosemont IL
21.41 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and ...

Sheraton Suites Chicago Elk Grove
121 Northwest Point Boulevard Elk Grove Village IL
18.69 km from city center
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woodfield Mall ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 19 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 20 hours ago
$216
Roundtrip
found 20 hours ago

Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago

Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago

Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago

Tue, Aug 11 - Sat, Aug 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$286 Roundtrip, found 2 days ago
$286
Roundtrip
found 2 days ago

