| Price | From | Airline | Dates | Details |
|---|---|---|---|---|
| $58 RT Book Now |
Minneapolis, MN MSP (arrives ORD) |
 Spirit Airlines |
May 25, 2013 - Aug 31, 2013 Sale ends today |
$9 Fare Club Member Fares. |
| $98 RT Book Now |
Myrtle Beach, SC MYR (arrives ORD) |
Spirit Airlines |
May 25, 2013 - Aug 31, 2013 Sale ends today |
$9 Fare Club Member Fares. |
| $118 RT Book Now |
Trenton, NJ TTN (arrives MDW) |
 Frontier |
May 23, 2013 - May 28, 2013 Sale ends in 6 days |
Flights to/from the Trenton/Princeton Area. |
| $118 RT Book Now |
Houston, TX IAH (arrives ORD) |
Spirit Airlines |
May 25, 2013 - Aug 31, 2013 Sale ends today |
$9 Fare Club Member Fares. |
| $126 RT Book Now |
Denver, CO DEN (arrives MDW) |
 Southwest |
Jun 4, 2013 - Jun 25, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $138 RT Book Now |
Denver, CO DEN (arrives MDW) |
Frontier |
May 23, 2013 - May 28, 2013 Sale ends in 6 days |
Fights between 20+ US Cities. |
| $138 RT Book Now |
Ft. Lauderdale, FL FLL (arrives ORD) |
Spirit Airlines |
May 25, 2013 - Aug 31, 2013 Sale ends today |
$9 Fare Club Member Fares. |
| $140 RT Book Now |
Denver, CO DEN (arrives MDW) |
Southwest |
Aug 26, 2013 - Dec 18, 2013 Sale ends in 1 day |
Travel Monday through Thursday and Saturday. |
| $148 RT Book Now |
Minneapolis, MN MSP (arrives ORD) |
 Sun Country Air |
Through Aug 28, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $161 RT Book Now |
Cincinnati, OH CVG (arrives ORD) |
 United |
May 24, 2013 - May 28, 2013 Sale ends in 2 days |
Depart 5/24/13 - 5/25/13. Return Monday or Tuesday. |
| $161 RT Book Now |
Green Bay, WI GRB (arrives ORD) |
United |
May 24, 2013 - May 28, 2013 Sale ends in 2 days |
Depart 5/24/13 - 5/25/13. Return Monday or Tuesday. |
| $174 RT Book Now |
Denver, CO DEN (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $198 RT Book Now |
Wichita, KS ICT (arrives MDW) |
Southwest |
Through Nov 1, 2013 |
14 Day Advance Purchase Required. |
| $202 RT Book Now |
New York City, NY LGA (arrives MDW) |
Southwest |
Aug 26, 2013 - Dec 18, 2013 Sale ends in 1 day |
Travel Monday through Thursday and Saturday. |
| $202 RT Book Now |
Boston, MA BOS (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $202 RT Book Now |
Boston, MA BOS (arrives MDW) |
Southwest |
Jun 4, 2013 - Jun 25, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $204 RT Book Now |
Cleveland, OH CLE (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $204 RT Book Now |
Columbus, OH CMH (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $220 RT Book Now |
Atlanta, GA ATL (arrives MDW) |
Southwest |
Aug 26, 2013 - Dec 18, 2013 Sale ends in 1 day |
Travel Monday through Thursday and Saturday. |
| $262 RT Book Now |
Washington DC, DC DCA (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $270 RT Book Now |
Houston, TX IAH (arrives ORD) |
United |
May 24, 2013 - May 28, 2013 Sale ends in 2 days |
Depart 5/24/13 - 5/25/13. Return Monday or Tuesday. |
| $274 RT Book Now |
Atlanta, GA ATL (arrives MDW) |
 AirTran |
Jun 4, 2013 - Jun 25, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $282 RT Book Now |
Washington DC, DC IAD (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $292 RT Book Now |
Charlotte, NC CLT (arrives MDW) |
Southwest |
Aug 26, 2013 - Dec 18, 2013 Sale ends in 1 day |
Travel Monday through Thursday and Saturday. |
| Las Vegas, NV LAS (arrives ORD) |
 Via Travelocity |
May 28, 2013 - Jun 15, 2013 |
7 Day Advance Purchase Required. |
|
| $298 RT Book Now |
Dallas, TX DFW (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $304 RT Book Now |
Ft. Lauderdale, FL FLL (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $306 RT Book Now |
San Antonio, TX SAT (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $308 RT Book Now |
Atlanta, GA ATL (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $315 RT Book Now |
Houston, TX IAH (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $316 RT Book Now |
Austin, TX AUS (arrives MDW) |
Southwest |
Aug 26, 2013 - Dec 18, 2013 Sale ends in 1 day |
Travel Monday through Thursday and Saturday. |
| $316 RT Book Now |
Austin, TX AUS (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $316 RT Book Now |
Tampa, FL TPA (arrives MDW) |
AirTran |
Jun 4, 2013 - Jun 25, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $320 RT Book Now |
New Orleans, LA MSY (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $327 RT Book Now |
Las Vegas, NV LAS (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $332 RT Book Now |
Orlando, FL MCO (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $338 RT Book Now |
Jacksonville, FL JAX (arrives MDW) |
Southwest |
Through Nov 1, 2013 |
14 Day Advance Purchase Required. |
| $344 RT Book Now |
Toronto, ON, Canada YYZ (arrives ORD) |
 Porter Airlines |
Through Sep 3, 2013 Sale ends in 2 days |
14 Day Advance Purchase Required. |
| $346 RT Book Now |
Phoenix, AZ PHX (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $351 RT Book Now |
Charlotte, NC CLT (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $358 RT Book Now |
Los Angeles, CA LAX (arrives ORD) |
 Virgin America |
Jun 1, 2013 - Nov 20, 2013 Sale ends in 7 days |
10 - 14 Day Advance Purchase Required. |
| $358 RT Book Now |
San Francisco, CA SFO (arrives ORD) |
Virgin America |
Jun 1, 2013 - Nov 20, 2013 Sale ends in 7 days |
10 - 14 Day Advance Purchase Required. |
| $366 RT Book Now |
West Palm Beach, FL PBI (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $376 RT Book Now |
Tampa, FL TPA (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $386 RT Book Now |
Ft. Lauderdale, FL FLL (arrives MDW) |
AirTran |
Jun 4, 2013 - Jun 25, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $391 RT Book Now |
San Francisco, CA SFO (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $398 RT Book Now |
New York City, NY LGA (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $398 RT Book Now |
Las Vegas, NV LAS (arrives MDW) |
Southwest |
Jun 4, 2013 - Jun 25, 2013 Sale ends in 1 day |
14 Day Advance Purchase Required. |
| $406 RT Book Now |
Santa Ana, CA SNA (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $411 RT Book Now |
Portland, OR PDX (arrives ORD) |
United |
Through Dec 31, 2013 |
Flights to Chicago from 15+ US Cities. |
| $482 RT Book Now |
Montreal, QC, Canada YUL (arrives ORD) |
Porter Airlines |
Through Sep 3, 2013 Sale ends in 2 days |
14 Day Advance Purchase Required. |
| $532 RT Book Now |
Ottawa, ON, Canada YOW (arrives ORD) |
Porter Airlines |
Through Sep 3, 2013 Sale ends in 2 days |
14 Day Advance Purchase Required. |
| $542 RT Book Now |
Moncton, NB, Canada YQM (arrives MDW) |
Porter Airlines |
Through Sep 3, 2013 Sale ends in 2 days |
14 Day Advance Purchase Required. |
| $554 RT Book Now |
Halifax, NS, Canada YHZ (arrives ORD) |
Porter Airlines |
Through Sep 3, 2013 Sale ends in 2 days |
14 Day Advance Purchase Required. |
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