
$70 Cheap flight deals from Boston (BOS) to Deerfield (CHI)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from Boston to Deerfield
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $70 One Way, $135 Round Trip from Boston to Deerfield
Prices starting at $135 for return flights and $70 for one-way flights to Deerfield were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Deerfield economy flight packages

Eurostars Magnificent Mile
May 22 - May 24
Boston (BOS) to Chicago (ORD)
Reviewed on Oct 18, 2025

Fairmont Chicago at Millennium Park
May 23 - May 25
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 16, 2026

Hilton Garden Inn Chicago Downtown South Loop
May 22 - May 26
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 18, 2026
Deerfield first class flight packages

Eurostars Magnificent Mile
May 21 - May 25
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Oct 18, 2025

Fairmont Chicago at Millennium Park
May 21 - May 25
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 16, 2026

Trump International Hotel & Tower Chicago
May 21 - May 25
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Oct 13, 2025
More About Flying To Deerfield from Boston
Route Information for Flights from Boston to Deerfield
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Deerfield
Planning a romantic getaway, traveling the world at last or flying out to see the kids and grandkids? Orbitz On-the-Go saves you both time and money. Our cutting edge mobile tools and guaranteed low prices leave plenty of room in your budget for the important things in life. Find same-day deals on domestic flights from Boston to Deerfield, and bargain sales on international Boston to Deerfield flights.
Family Matters, and So Do Cheap Tickets
Don’t miss another birthday, graduation or wedding, wherever they are. Take advantage of Orbitz On-the-Go’s discount travel planning features to save on flights from Boston to Deerfield and Boston to Deerfield flights. Tell them you’ll be there, every single time.
Escape to Romance
Treat yourself and the one you love to a romantic hideaway. Orbitz budget air flights from Boston to Deerfield and Boston to Deerfield flights can be bundled into packages for extravagant savings at spa resorts and hotels.
See the World
It’s finally your time. Go wherever the wind takes you. Orbitz On-the-Go makes dreams come true. Book low fare flights from Boston to Deerfield, the world is at your fingertips.
Flight or Gate Changes? No Problem
Once you’ve reserved your low cost air ticket on Boston to Deerfield flights or flights from Boston to Deerfield, stay informed with Orbitz On-the-Go free alerts. Choose from email, voice and text notification. You’ll always know your flight status and gate number, and where and how to pick up your bags.
Flights from Boston
- Boston to Orlando
- Boston to London
- Boston to Chicago
- Boston to Los Angeles
- Boston to Miami
- Boston to New York
- Boston to Paris
- Boston to Atlanta
- Boston to Toronto
- Boston to Houston
- Boston to Dallas
- Boston to Rome
- Boston to Madrid
- Boston to Montreal
- Boston to Detroit
- Boston to Buenos Aires
- Boston to Beijing
- Boston to Sao Paulo
- Boston to Kansas City
- Boston to Berlin
More Destinations
- Flights from Guadalajara to Highland Park
- Flights from Dallas to Highland Park
- Flights from Houston to Highland Park
- Flights from Los Angeles to Highland Park
- Flights from Mexico City to Highland Park
- Flights from Miami to Highland Park
- Flights from Minneapolis - St. Paul to Highland Park
- Flights from New York to Highland Park
- Flights from Phoenix to Highland Park
- Flights from San Antonio to Highland Park
- Flights from San Francisco to Highland Park
- Flights from Seattle to Highland Park
- Flights from Toronto to Highland Park
- Flights from Tampa to Highland Park
- Flights from Austin (AUS) to Chicago (ORD)
- Flights from Nashville (BNA) to Chicago (ORD)
- Flights from Boise (BOI) to Chicago (ORD)
- Flights from Boston (BOS) to Chicago (ORD)
- Flights from Charleston (CHS) to Chicago (ORD)
- Flights from Cedar Rapids (CID) to Chicago (ORD)
- Flights from Charlotte (CLT) to Chicago (ORD)
- Flights from Columbus (CMH) to Chicago (ORD)
- Flights from Columbia (COU) to Chicago (ORD)
- Flights from Cincinnati (CVG) to Chicago (ORD)
- Flights from Dallas (DAL) to Chicago (ORD)
- Flights from Delhi (DEL) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Des Moines (DSM) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Dubai (DXB) to Chicago (ORD)
- Flights from Grand Rapids (GRR) to Chicago (ORD)
- Flights from White Plains (HPN) to Chicago (ORD)
- Flights from Seoul (ICN) to Chicago (ORD)
- Flights from Jacksonville (JAX) to Chicago (ORD)
- Flights from Chennai (MAA) to Chicago (ORD)
- Flights from Kansas City (MCI) to Chicago (ORD)
- Flights from Harrisburg (MDT) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Milwaukee (MKE) to Chicago (ORD)
- Flights from Madison (MSN) to Chicago (ORD)
- Flights from Ontario (ONT) to Chicago (ORD)
- Flights from West Palm Beach (PBI) to Chicago (ORD)
- Flights from Portland (PDX) to Chicago (ORD)
- Flights from Beijing (PEK) to Chicago (ORD)
- Flights from Peoria (PIA) to Chicago (ORD)
- Flights from Pittsburgh (PIT) to Chicago (ORD)
- Flights from Shanghai (PVG) to Chicago (ORD)
- Flights from San Diego (SAN) to Chicago (ORD)
- Flights from San Antonio (SAT) to Chicago (ORD)
- Flights from Savannah (SAV) to Chicago (ORD)
- Flights from Louisville (SDF) to Chicago (ORD)
- Flights from San Jose (SJC) to Chicago (ORD)
- Flights from Salt Lake City (SLC) to Chicago (ORD)
- Flights from Sacramento (SMF) to Chicago (ORD)
- Flights from St. Louis (STL) to Chicago (ORD)
- Flights from Trenton (TTN) to Chicago (ORD)
- Flights from Knoxville (TYS) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Atlanta to Chicago
- Flights from Boston to Chicago
- Flights from Dallas to Chicago
- Flights from Houston to Chicago
- Flights from New York to Chicago
- Flights from Atlanta to Des Plaines
- Flights from Boston to Des Plaines
- Flights from Charlotte to Des Plaines
- Flights from Dallas to Des Plaines
- Flights from Denver to Des Plaines
- Flights from Las Vegas to Des Plaines
- Flights from Miami to Des Plaines
- Flights from Orlando to Des Plaines
- Flights from Philadelphia to Des Plaines
- Flights from Toronto to Des Plaines
- Flights from Jacksonville to Des Plaines
- Flights from Mexico City to Arlington Heights
- Flights from Miami to Arlington Heights
- Flights from Jacksonville to Arlington Heights
- Flights from Zhengzhou to Arlington Heights
- Flights from Boston to Glenview
- Flights from Houston to Glenview
- Flights from Miami to Glenview
- Flights from Tampa to Glenview
- Flights from Beijing to Evanston
- Flights from Miami to Evanston
- Flights from Orlando to Evanston
- Flights from Portland to Evanston
- Flights from Raleigh to Evanston
- Flights from Fort Lauderdale to Evanston
- Flights from Savannah to Evanston
- Flights from Boston to Northbrook
- Flights from Dallas to Northbrook
- Flights from Denver to Northbrook
- Flights from Houston to Northbrook
- Flights from Jakarta to Northbrook
- Flights from Miami to Northbrook
- Flights from Minneapolis - St. Paul to Northbrook
- Flights from New Orleans to Northbrook
- Flights from Philadelphia to Northbrook
- Flights from Phoenix to Northbrook
- Flights from Hartford to Northbrook
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.




